WO2011126917A1 - Monophosphorus ligands and their use in cross-coupling reactions - Google Patents

Monophosphorus ligands and their use in cross-coupling reactions Download PDF

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Publication number
WO2011126917A1
WO2011126917A1 PCT/US2011/030681 US2011030681W WO2011126917A1 WO 2011126917 A1 WO2011126917 A1 WO 2011126917A1 US 2011030681 W US2011030681 W US 2011030681W WO 2011126917 A1 WO2011126917 A1 WO 2011126917A1
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WIPO (PCT)
Prior art keywords
dihydrobenzo
membered
cio
alkyl
oxaphosphole
Prior art date
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Ceased
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PCT/US2011/030681
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English (en)
French (fr)
Inventor
Nizar Haddad
Bo QU
Sonia Rodriguez
Chris Senanayake
Wenjun Tang
Xudong Wei
Nathan K. Yee
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Boehringer Ingelheim International GmbH
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Boehringer Ingelheim International GmbH
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Priority to JP2013503796A priority Critical patent/JP5803042B2/ja
Priority to US13/635,671 priority patent/US9096626B2/en
Priority to EP20110715332 priority patent/EP2556077B1/en
Publication of WO2011126917A1 publication Critical patent/WO2011126917A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/04—Substitution
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide

Definitions

  • the present invention relates to a series of novel P-chiral monophosphorus ligands derived from a dihydrobenzo[l,3]oxaphosphole framework and their metal complexes as catalysts for applications in cross-coupling reaction. More particularly, the present invention relates to these phosphine ligands and their related catalysts for transition metal catalyzed cross- coupling reactions including carbon-carbon bond forming reactions and C-X cross- coupling reactions.
  • Metal-catalyzed cross-coupling has become one of the most important transformations in organic chemistry.
  • Development of efficient chiral or nonchiral ligands for metal-catalyzed cross-coupling has gained particular attention in the latest twenty years.
  • the Suzuki-Miyaura coupling has become one of most useful method for formation of carbon-carbon bonds and has been used in numerous synthetic ventures. (N. Miyaura, Topics in Current Chem. 2002, 219, 11 ; A. Suzuki, Organomet. Chem. 1999, 576, 147). Despite the recent advances on this reaction, the Suzuki-Miyaura coupling of sterically hindered substrates and further decrease of the catalyst loading remain great challenges. Development of new ligands for Suzuki-Miyaura coupling reaction remains imperative to further increase its efficiency and expand its substrate scope.
  • the invention provides a series of novel and efficient chiral monophosphorus ligands derived from a dihydrobenzo[l ,3]oxaphosphole framework that has shown superior results for Suzuki coupling or asymmetric Suzuki reaction. High reactivity and selectivity have been observed in a sterically-congested asymmetric Suzuki coupling.
  • the present invention provides compounds of the formula (la), (lb), or a mixture thereof:
  • R is (Ci-C6)-alkyl, CF 3 , (C3-Cio)-carbocyclyl, (5- to l l-membered)heterocarbocyclyl, (C6-Cio)aryl, (5 to 11 -membered)heteroaryl, or ferrocenyl, wherein each such (C3-C6)-alkyl, CF 3 , (C3-Cio)-carbocyclyl, (5- to l l-membered)heterocarbocyclyl, (C6-Cio)aryl, (5 to 11 -membered)heteroaryl, or ferrocenyl, wherein each such (C3-
  • Cio)carbocyclyl, (5- to l l-membered)heterocarbocyclyl, (C6-Cio)aryl or (5 to 11- membered)heteroaryl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of -0(Ci-C6)alkyl, (Ci-C6)alkyl, and CF 3 ;
  • R 1 , R 2 , R 3 , R 4 , R 5 are each independently selected from the group consisting of H, halo, CF 3 , -0(Ci-C 6 )alkyl, (Ci-C 6 )alkyl, (C 3 -Ci 0 )carbocyclyl, (5- to 11- membered)heterocarbocyclyl, (C6-Cio)aryl, (5 to 11 -membered)heteroaryl, -NR n R 12 , - Si(R n )3 and -SR 11 , wherein each such (C3-Cio)carbocyclyl, (5- to I lmembered)heterocarbocyclyl, (C6-Cio)aryl or (5 to 1 l-membered)heteroaryl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of -0(Ci-C6)alkyl,
  • R 11 and R 12 are each independently selected from the group consisting of H, (Ci- C 6 )alkyl, CF 3 , (C3-Cio)carbocyclyl, (5- to l l-membered)heterocarbocyclyl, (C 6 - Cio)aryl, and (5 to l l-membered)heteroaryl, wherein each such (C3-Cio)carbocyclyl, (5- to l l-membered)heterocarbocyclyl, (C6-Cio)aryl or (5 to 11 -membered)heteroaryl group is optionally independently substituted with 1 to 3 substituents independently selected from the group consisting of halo, -0(Ci-C6)alkyl, (Ci-C6)alkyl, and -CF 3 .
  • the invention relates to compounds of formula (la), (lb), or a mixture thereof, wherein R is -(Ci-C6)alkyl selected from -CH 3 , -CH 2 CH 3 , -CH(CH 3 ) 2 ,
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R n and R 12 are as defined in the first aspect.
  • the invention provides compounds of the formula (la), (lb), or a mixture thereof, wherein R is -(C3-Cio)carbocyclyl selected from cyclopentyl, cyclohexyl, and 1-adamantyl, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are as defined in the first aspect.
  • the invention provides compounds of the formula (la), (lb), or a mixture thereof, wherein R is -(C 6 -Cio)aryl selected from phenyl, ortho-tolyl, para- tolyl, 3,5-dimethylphenyl, 3,5-di-i-butylphenyl, 3,5-di-CF 3 -phenyl, ortho-CF 3 -phenyl, ortho-anisyl, and naphthyl, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are as defined in the first aspect.
  • the invention provides compounds of the formula (la), (lb), or a mixture thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 are each independently H, -CH 3 , -CH 2 CH 3 ,
  • R, R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are as defined in the first, second, third or fourth aspect.
  • the invention provides compounds of the formula (la), (lb), or a mixture thereof, wherein R 6 , R 7 , R 8 are H, and R, R 1 , R 2 , R 3 , R 4 , R 5 , R 9 , R 10 , R 11 and R 12 are as defined in the first, second, third, fourth or fifth aspect.
  • the invention provides compounds of the formula (la), (lb), or a mixture thereof, R 9 and R 10 are each independently H, -CH , -CH 2 CH , -CH(CH ) 2 ,
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 and R 12 are as defined in the first, second, third, fourth, fifth aspect or sixth aspect.
  • the invention provides a phosphine ligand having the formula (Ila) or (lib), or a mixture thereof,
  • R is -CH(CH 3 ) 2 , -C(CH 3 ) 3 -C(CH 2 CH 3 )(CH 3 ) 2, cyclohexyl, 1 -adamantyl, phenyl, ortho- tolyl, 3,5-xylyl, ortho-anisyl, or ferrocenyl; and R 1 , R 2 , and R 3 are independently H, -CH 3 , -CH 2 CH 3 , -CH(CH 3 ) 2 , -C(CH 3 ) 3 , -OCH 3 , -OCH 2 CH 3, -OCH(CH 3 ) 2 , OPh, N(CH 3 ) 2 , N(CH 2 CH 3 ) 2 , SiMe 3 , CF 3 .
  • phosphine ligands selected from the group consisting of:
  • the present invention further provides a catalyst prepared by a process including contacting a transition metal salt, or a complex thereof, and a chiral ligand according to the present invention as described.
  • the present invention further provides a process for preparation of a chiral or nonchiral compound by employing a ligand or catalyst according to the present invention as described herein above.
  • the present invention provides a process for preparation of the above- described ligands of formulas la, lb, Ila and lib.
  • these ligands may be prepared in the manner depicted in the general reaction scheme below.
  • phenol Ilia or its enantiomer, or a mixture of thereof is converted into a triflate IVa, or its enantiomer, or a mixture of thereof, by reacting with Tf 2 NPh or trifluoromethylsulfonyl anhydride in a suitable solvent such as
  • Example 1 (5 , )-3-ieri-butyl-2,3-dihydrobenzo[ ⁇ i][l,3]oxaphosphol-4-yl trifluoromethanesulfonate oxide
  • the CH 2 C1 2 layer was separated, dried over sodium sulfate, concentrated, and purified by silica gel column chromatography (eluents: hexanes to EtOAc) to provide (5)-3-ieri-butyl-2,3- dihydrobenzo[ ⁇ i][l,3]oxaphosphol-4-yl trifluoromethanesulfonate oxide (75 mg, 0.21 mmol, 95%) as white solid.
  • Example 3 (5')-3-tert-butyl-4-(2,6-dimethoxyphenyl)-2,3- dihydrobenzo[if
  • the MTBE layer was separated and the aqueous layer was washed with MTBE under nitrogen.
  • the MTBE solution was dried, concentrated, and purified by passing through a neutral alumina plug to give the desired product as white crystalline solid (5 g, 15.1 mmol, 81%).
  • Example 5 (5')-3-ieri-butyl-4-phenyl-2,3-dihydrobenzo[if
  • Example 12 (/?)-3-tert-butyl-4-(2,6-diisopropoxyphenyl)-2,3- dihydrobenzo[if

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/US2011/030681 2010-04-05 2011-03-31 Monophosphorus ligands and their use in cross-coupling reactions Ceased WO2011126917A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2013503796A JP5803042B2 (ja) 2010-04-05 2011-03-31 クロスカップリング反応におけるモノリン配位子及びそれらの使用
US13/635,671 US9096626B2 (en) 2010-04-05 2011-03-31 Monophosphorus ligands and their use in cross-coupling reactions
EP20110715332 EP2556077B1 (en) 2010-04-05 2011-03-31 Monophosphorus ligands and their use in cross-coupling reactions

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US61/320,871 2010-04-05

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104558038A (zh) * 2013-10-23 2015-04-29 中国科学院上海有机化学研究所 一种取代的2,3-二氢苯并[d][1,3]氧杂磷杂茂配体的制备方法
WO2018035685A1 (en) 2016-08-22 2018-03-01 Basf Se Process for preparing substituted biphenyls
WO2018106746A3 (en) * 2016-12-06 2018-07-19 Boehringer Ingelheim International Gmbh Novel chiral dihydrobenzooxaphosphole ligands and synthesis thereof
WO2019170163A1 (zh) 2018-03-07 2019-09-12 东莞市均成高新材料有限公司 三联芳单膦配体、它们的制备方法和在催化偶联反应中的用途
WO2025103462A1 (en) * 2023-11-17 2025-05-22 Shenzhen Catalys Technology Co., Ltd Substituted 2, 3-dihydrobenzo [d] [1, 3] oxaphosphole ligand, preparation method and use thereof

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US9394387B2 (en) 2014-05-15 2016-07-19 Chevron Phillips Chemical Company Lp Synthesis of aryl coupled bis phenoxides and their use in olefin polymerization catalyst systems with activator-supports
EP3408253A1 (en) 2016-01-28 2018-12-05 Acatechol, Inc. Photo-cleavable primer compositions and methods of use
EP3551639B1 (en) * 2016-12-06 2023-08-23 Boehringer Ingelheim International GmbH Novel chiral dihydrobenzoazaphosphole ligands and synthesis thereof
CN107827929B (zh) * 2017-11-17 2020-03-10 中国科学院上海有机化学研究所 一种联芳基双膦配体、其制备方法及应用

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104558038A (zh) * 2013-10-23 2015-04-29 中国科学院上海有机化学研究所 一种取代的2,3-二氢苯并[d][1,3]氧杂磷杂茂配体的制备方法
WO2018035685A1 (en) 2016-08-22 2018-03-01 Basf Se Process for preparing substituted biphenyls
IL264681B (en) * 2016-08-22 2021-10-31 Basf Se Process for preparing substituted biphenyls
WO2018106746A3 (en) * 2016-12-06 2018-07-19 Boehringer Ingelheim International Gmbh Novel chiral dihydrobenzooxaphosphole ligands and synthesis thereof
US10221203B2 (en) 2016-12-06 2019-03-05 Boehringer Ingelheim International Gmbh Chiral dihydrobenzooxaphosphole ligands and synthesis thereof
US10544177B2 (en) 2016-12-06 2020-01-28 Boehringer Ingelheim International Gmbh Chiral dihydrobenzooxaphosphole ligands and synthesis thereof
WO2019170163A1 (zh) 2018-03-07 2019-09-12 东莞市均成高新材料有限公司 三联芳单膦配体、它们的制备方法和在催化偶联反应中的用途
WO2025103462A1 (en) * 2023-11-17 2025-05-22 Shenzhen Catalys Technology Co., Ltd Substituted 2, 3-dihydrobenzo [d] [1, 3] oxaphosphole ligand, preparation method and use thereof

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EP2556077B1 (en) 2014-03-19
JP5803042B2 (ja) 2015-11-04
US20130137902A1 (en) 2013-05-30
EP2556077A1 (en) 2013-02-13
JP2013523813A (ja) 2013-06-17
US9096626B2 (en) 2015-08-04

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