JP2017531635A - フルオロスルホネート化合物をアミン化合物にカップリングさせるための方法 - Google Patents
フルオロスルホネート化合物をアミン化合物にカップリングさせるための方法 Download PDFInfo
- Publication number
- JP2017531635A JP2017531635A JP2017517238A JP2017517238A JP2017531635A JP 2017531635 A JP2017531635 A JP 2017531635A JP 2017517238 A JP2017517238 A JP 2017517238A JP 2017517238 A JP2017517238 A JP 2017517238A JP 2017531635 A JP2017531635 A JP 2017531635A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- palladium
- group
- ligand
- acetate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/04—Formation or introduction of functional groups containing nitrogen of amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/66—Preparation of compounds containing amino groups bound to a carbon skeleton from or via metallo-organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/90—Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/48—N-alkylated amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/44—Allylic alkylation, amination, alkoxylation or analogues
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
本実施例において、式5に示すように、パラ−トリルスルフロフルオリデートを、ジフェニルアミンと反応させる。
本実施例において、式6に示すように、p−トリルスルフロフルオリデートを、ベンジルアミンと反応させる。
本実施例において、式7に示すように、アリールフルオロスルホネートを、アニリンと反応させる。
本実施例において、式8に示すように、アリールフルオロスルホネートを、アニリンと反応させる。
本実施例において、式9に示すように、エチル−4−ヒドロキシベンゾエートをアニリンにカップリングさせるためにワンポット合成を提供する。
本実施例において、式10に示すように、アリールフルオロスルホネートを、モルフォリンと反応させる。
Claims (20)
- 第1の化合物を第2の化合物にカップリングさせる方法であって、
フルオロスルホン酸置換基を有する前記第1の化合物を提供することであって、前記第1の化合物が、アリールまたはヘテロアリール基を含む、提供することと、
アミンを含む前記第2の化合物を提供することと、
前記第1の化合物と前記第2の化合物とを、反応混合物中で反応させることであって、前記反応混合物が、少なくとも1つの10族原子を有する触媒を含み、前記反応混合物が、前記第1の化合物を前記第2の化合物にカップリングさせるのに有効な条件下にある、反応させることと、を含む、方法。 - 前記反応混合物が、配位子をさらに含む、請求項1に記載の方法。
- 前記触媒が、パラジウムプレ触媒からその場で生成される、請求項1または2に記載の方法。
- 前記触媒が、パラジウムプレ触媒からその場で生成され、前記パラジウムプレ触媒が、酢酸パラジウム(II)、塩化パラジウム(II)、ジクロロビス(アセトニトリル)パラジウム(II)、ジクロロビス(ベンゾニトリル)パラジウム(II)、アリルパラジウムクロリド二量体、パラジウム(II)アセチルアセトネート、臭化パラジウム(II)、ビス(ジベンジリデンアセトン)パラジウム(0)、ビス(2−メチルアリル)パラジウムクロリド二量体、クロチルパラジウムクロリド二量体、ジクロロ(1,5−シクロオクタジエン)パラジウム(II)、ジクロロ(ノルボルナジエン)パラジウム(II)、トリフルオロ酢酸パラジウム(II)、安息香酸パラジウム(II)、トリメチル酢酸パラジウム(II)、酸化パラジウム(II)、シアン化パラジウム(II)、トリス(ジベンジリデンアセトン)ジパラジウム(0)、パラジウム(II)ヘキサフルオロアセチルアセトネート、シス−ジクロロ(N,N,N’,N’−テトラメチルエチレンジアミン)パラジウム(II)、及びシクロペンタジエニル[(1,2,3−n)−1−フェニル−2−プロペニル]パラジウム(II)、[1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾール−2−イリデン](3−クロロピリジル)パラジウム(II)ジクロリド、及び(1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾリデン)(3−クロロピリジル)パラジウム(II)ジクロリド、ならびにこれらのうちの2つ以上の混合物からなる群から選択される、請求項1〜3のいずれか一項に記載の方法。
- 前記配位子が、ホスフィン配位子またはカルベン配位子である、請求項1〜4のいずれか一項に記載の方法。
- 前記配位子が、アミン系配位子、アミノホスフィン系配位子、N−複素環式カルベン系配位子、一座もしくは二座アルキルアミン、または一座もしくは二座芳香族アミンである、請求項1〜5のいずれか一項に記載の方法。
- 前記反応混合物が、塩基を含む、請求項1〜6のいずれか一項に記載の方法。
- 前記塩基が、炭酸塩、リン酸塩、酢酸塩、アルコキシド塩、またはカルボン酸塩である、請求項7に記載の方法。
- 前記塩基が、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸ルビジウム、炭酸セシウム、炭酸アンモニウム、置換炭酸アンモニウム、炭酸水素塩、リン酸リチウム、リン酸ナトリウム、リン酸カリウム、リン酸ルビジウム、リン酸セシウム、リン酸アンモニウム、置換リン酸アンモニウム、リン酸水素塩、酢酸リチウム、酢酸ナトリウム、酢酸カリウム、酢酸ルビジウム、酢酸セシウム、酢酸アンモニウム、置換酢酸アンモニウム、リチウム、ナトリウム、カリウム、ルビジウム、セシウム、アンモニウム、及び置換アンモニウムカチオンとの、ギ酸塩、フルオロ酢酸塩、プロピオン酸アニオン、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、マグネシウムジヒドロキシド、カルシウムジヒドロキシド、ストロンチウムジヒドロキシド、及びバリウムジヒドロキシド、アルミニウムトリヒドロキシド、ガリウムトリヒドロキシド、インジウムトリヒドロキシド、タリウムトリヒドロキシド、トリエチルアミン、N,N−ジイソプロピルエチルアミン、1,4−ジアザビシクロ[2.2.2]オクタン、1,5−ジアザビシクロ[4.3.0]ノナ−5−エン、1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エン、ビス(トリメチルシリル)アミドのリチウム、ナトリウム、及びカリウム塩、tブトキシドのリチウム、ナトリウム、及びカリウム塩、1,8−ビス(ジメチルアミノ)ナフタレン、ピリジン、モルフォリン、2,6−ルチジン、トリエチルアミン、N,N−ジシクロヘキシルメチルアミン、ジイソプロピルアミン、フッ化ナトリウム、フッ化カリウム、フッ化セシウム、フッ化銀、フッ化テトラブチルアンモニウム、フッ化アンモニウム、フッ化トリエチルアンモニウム、ならびにこれらのうちの2つ以上の混合物からなる群から選択される、請求項7または8に記載の方法。
- 反応混合物が、溶媒を含む、請求項1〜9のいずれか一項に記載の方法。
- 前記溶媒が、トルエン、キシレン、ベンゼン、クロロベンゼン、水、メタノール、エタノール、1−プロパノール、2−プロパノール、n−ブタノール、2−ブタノール、ペンタノール、ヘキサノール、tert−ブチルアルコール、tert−アミルアルコール、エチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、グリセロール、N−メチル−2−ピロリドン、アセトニトリル、N,N−ジメチルホルムアミド、酢酸メチル、酢酸エチル、酢酸プロピル、酢酸イソプロピル、トリアセチン、アセトン、メチルエチルケトン、及び1,4−ジオキサン、テトラヒドロフラン、2−メチルテトラヒドロフラン、ジエチルエーテル、シクロペニルメチルエーテル、2−ブチルエチルエーテル、ジメトキシエタン、ポリエチレングリコールなどのエーテル系溶媒、ジメチルアセトアミド(DMA)、ジメチルスルホキシド(DMSO)、及び1,2−ジクロロエタン(DCE)からなる群から選択される、請求項10に記載の方法。
- 前記反応混合物が、水を含む、請求項1〜11のいずれか一項に記載の方法。
- 式1に示されるように、第1の化合物A1を第2の化合物A2にカップリングさせる方法であって、
10族原子を含む触媒及び第2の化合物A2を、前記反応混合物に提供することであって、前記第2の化合物A2が、式4で定義される通りであり、
前記第1の化合物を前記第2の化合物にカップリングさせるのに有効な条件下で、前記第1の化合物及び前記第2の化合物を反応させることと、を含む、方法。 - 前記反応混合物が、配位子、及び塩基をさらに含む、請求項13に記載の方法。
- 前記触媒が、パラジウムプレ触媒からその場で生成される、請求項13または14に記載の方法。
- 前記配位子が、ホスフィン配位子またはカルベン配位子である、請求項13〜15のいずれか一項に記載の方法。
- 前記配位子が、アミン系配位子、アミノホスフィン系配位子、またはN−複素環式カルベン系配位子である、請求項13〜16のいずれか一項に記載の方法。
- 前記配位子が、一座もしくは二座アルキルアミン、または一座もしくは二座芳香族アミンである、請求項13〜17のいずれか一項に記載の方法。
- 前記塩基が、炭酸塩、リン酸塩、酢酸塩、またはカルボン酸塩である、請求項13〜18のいずれか一項に記載の方法。
- 前記反応混合物が、溶媒を含む、請求項13〜19のいずれか一項に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462061641P | 2014-10-08 | 2014-10-08 | |
US62/061,641 | 2014-10-08 | ||
US201562149237P | 2015-04-17 | 2015-04-17 | |
US62/149,237 | 2015-04-17 | ||
PCT/US2015/054653 WO2016057770A1 (en) | 2014-10-08 | 2015-10-08 | Method for coupling a fluorosulfonate compound with an amine compound |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2017531635A true JP2017531635A (ja) | 2017-10-26 |
Family
ID=54478949
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017517238A Pending JP2017531635A (ja) | 2014-10-08 | 2015-10-08 | フルオロスルホネート化合物をアミン化合物にカップリングさせるための方法 |
Country Status (7)
Country | Link |
---|---|
US (2) | US20170210695A1 (ja) |
EP (1) | EP3204351A1 (ja) |
JP (1) | JP2017531635A (ja) |
KR (1) | KR20170070043A (ja) |
CN (1) | CN107074736A (ja) |
BR (1) | BR112017006795A2 (ja) |
WO (1) | WO2016057770A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2021529207A (ja) * | 2018-07-04 | 2021-10-28 | メルク パテント ゲーエムベーハー | アリールアミンを製造するための方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR112018068100A2 (pt) * | 2016-03-15 | 2019-01-15 | Dow Global Technologies Llc | método para acoplar um primeiro composto a um segundo composto |
JP7413346B2 (ja) | 2019-03-06 | 2024-01-15 | 第一三共株式会社 | ピロロピラゾール誘導体 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013002040A1 (ja) * | 2011-06-29 | 2013-01-03 | セントラル硝子株式会社 | フルオロ硫酸芳香環エステル類の製造方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090137831A1 (en) * | 2007-11-28 | 2009-05-28 | E. I. Du Pont De Nemours And Company | Fluorinated Alkanesulfonic Acid Esters and Amides and Processes for Making and Using the Same |
-
2015
- 2015-10-08 US US15/515,071 patent/US20170210695A1/en not_active Abandoned
- 2015-10-08 CN CN201580053328.2A patent/CN107074736A/zh active Pending
- 2015-10-08 BR BR112017006795A patent/BR112017006795A2/pt not_active Application Discontinuation
- 2015-10-08 KR KR1020177009776A patent/KR20170070043A/ko unknown
- 2015-10-08 JP JP2017517238A patent/JP2017531635A/ja active Pending
- 2015-10-08 WO PCT/US2015/054653 patent/WO2016057770A1/en active Application Filing
- 2015-10-08 EP EP15791809.5A patent/EP3204351A1/en not_active Withdrawn
-
2019
- 2019-02-08 US US16/271,008 patent/US20190177265A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013002040A1 (ja) * | 2011-06-29 | 2013-01-03 | セントラル硝子株式会社 | フルオロ硫酸芳香環エステル類の製造方法 |
Non-Patent Citations (5)
Title |
---|
ADV. SYNTH CATAL., vol. 351,11−12, JPN6019021379, 2009, pages 1717 - 1721, ISSN: 0004195708 * |
CHEM SOC REV, vol. 40, JPN6019021384, 2011, pages 4963 - 4972, ISSN: 0004195712 * |
J. ORG. CHEM., vol. 71, JPN6019021383, 2006, pages 430 - 433, ISSN: 0004195711 * |
JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 576, JPN6019021380, 1999, pages 125 - 146, ISSN: 0004195709 * |
ORGANIC LETTERS, vol. 5, no. 9, JPN6019021381, 2003, pages 1479 - 1482, ISSN: 0004195710 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2021529207A (ja) * | 2018-07-04 | 2021-10-28 | メルク パテント ゲーエムベーハー | アリールアミンを製造するための方法 |
Also Published As
Publication number | Publication date |
---|---|
KR20170070043A (ko) | 2017-06-21 |
BR112017006795A2 (pt) | 2018-01-09 |
CN107074736A (zh) | 2017-08-18 |
WO2016057770A1 (en) | 2016-04-14 |
US20170210695A1 (en) | 2017-07-27 |
EP3204351A1 (en) | 2017-08-16 |
US20190177265A1 (en) | 2019-06-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3122707B1 (en) | Method for coupling a first aromatic compound to a second aromatic compound | |
US20190177265A1 (en) | Method for coupling a first compound to a second compound | |
US10125082B2 (en) | Method for coupling a first compound to a second compound | |
JP2019023307A (ja) | ポリアリールポリマーを形成する方法及びそれにより形成されたポリマー | |
JP2018525391A (ja) | 芳香族またはビニル系化合物をホウ素含有化合物にカップリングさせるための方法 | |
JP2018523669A (ja) | 芳香族化合物をアルキンにカップリングさせるための方法 | |
JP2014169273A (ja) | 環式芳香族化合物の製造方法 | |
JP2019508442A (ja) | 第1の化合物を第2の化合物にカップリングさせるための方法 | |
TWI614231B (zh) | 用於形成多炔基-芳烴的方法 | |
JP6147057B2 (ja) | 2−アリールインデン化合物の製造方法および触媒組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170531 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20170619 |
|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20170619 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20170904 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180921 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20190315 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20190315 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20190606 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190611 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20200121 |