CN109748829B - Preparation method of oxalyl sulfonyl hydrazide and application of oxalyl sulfonyl hydrazide in olefin sulphonation reaction - Google Patents
Preparation method of oxalyl sulfonyl hydrazide and application of oxalyl sulfonyl hydrazide in olefin sulphonation reaction Download PDFInfo
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 29
- -1 oxalyl sulfonyl Chemical group 0.000 title claims abstract description 28
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 239000007800 oxidant agent Substances 0.000 claims abstract description 4
- 230000001590 oxidative effect Effects 0.000 claims abstract description 4
- 238000007259 addition reaction Methods 0.000 claims abstract description 3
- 230000003647 oxidation Effects 0.000 claims abstract description 3
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract description 12
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 7
- 239000003513 alkali Substances 0.000 abstract description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- BBNUGJZCLZHILC-UHFFFAOYSA-N 1-(3-bromophenyl)-2-(4-methylphenyl)sulfonylethanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC(=O)C1=CC=CC(Br)=C1 BBNUGJZCLZHILC-UHFFFAOYSA-N 0.000 description 1
- JGMRIHQYBXLTGM-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-methylphenyl)sulfonylethanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC(=O)C1=CC=C(Br)C=C1 JGMRIHQYBXLTGM-UHFFFAOYSA-N 0.000 description 1
- UFXWUSAAGJDPOF-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-2-phenylpropan-2-ol Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC(C)(O)C1=CC=CC=C1 UFXWUSAAGJDPOF-UHFFFAOYSA-N 0.000 description 1
- KQJQPCJDKBKSLV-UHFFFAOYSA-N 1-bromo-3-ethenylbenzene Chemical compound BrC1=CC=CC(C=C)=C1 KQJQPCJDKBKSLV-UHFFFAOYSA-N 0.000 description 1
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 1
- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 description 1
- RFQXSRPFYWMUDV-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyl-1-phenylethanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC(=O)C1=CC=CC=C1 RFQXSRPFYWMUDV-UHFFFAOYSA-N 0.000 description 1
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
Abstract
The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a preparation method of a sulfuryl reagent oxalyl sulfonyl hydrazide and application of the sulfuryl reagent oxalyl sulfonyl hydrazide in an olefin sulphonation reaction. The invention provides a method for preparing oxalyl sulfonyl hydrazide by reacting aryl sulfonyl hydrazide with oxalyl chloride in the presence of alkali. In addition, the invention provides a novel method for preparing beta-keto sulfone or beta-hydroxy sulfone by using the reaction of oxalyl sulfonyl hydrazide and substituted olefin. The method takes substituted olefin and oxalyl sulfonyl hydrazide as raw materials, takes oxygen in the air as an oxidant, and generates beta-keto sulfone or beta-hydroxy sulfone through oxidation addition reaction in the presence of a catalyst.
Description
Technical Field
The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a preparation method of a sulfuryl reagent oxalyl sulfonyl hydrazide and application of the sulfuryl reagent oxalyl sulfonyl hydrazide in an olefin sulphonation reaction.
Background
Aryl sulfone is an important organic functional group, and related compounds are widely applied to the fields of organic chemistry and polymer chemistry, including fine chemicals, pharmaceutical and pesticide raw materials, resin/plastic raw materials, electronic information materials, optical materials and the like.
Common aryl sulphonation agents include aryl sulphinic acids, aryl sulphonyl chlorides, aryl sulphonyl hydrazides and the like. The preparation and related application of the oxalyl sulfonyl hydrazide related to the invention are not reported.
Disclosure of Invention
The invention aims to provide a preparation method of a sulfone-based reagent oxalyl sulfonyl hydrazide and a novel method for preparing beta-keto sulfone or beta-hydroxy sulfone by reacting the sulfone-based reagent oxalyl sulfonyl hydrazide with olefin.
The method for preparing the oxalyl sulfonyl hydrazide by reacting aryl sulfonyl hydrazide with oxalyl chloride adopts the following general formula, takes oxalyl chloride and sulfonyl hydrazide as raw materials, and prepares the oxalyl sulfonyl hydrazide in the presence of alkali, wherein the reaction formula is as follows:
wherein R is aryl, heteroaryl, aryl or heteroaryl with substituent.
Further, R is phenyl, naphthyl, anthryl, pyridyl, furyl, thienyl, pyrrolyl or quinolyl with substituent groups.
The mass ratio of the oxalyl chloride to the sulfonyl hydrazide derivative is 1: 2; the mass ratio of oxalyl chloride to base is 1: 2.
The alkali is organic alkali, and the solvent used in the reaction is one or more of toluene, tetrahydrofuran, diethyl ether, acetonitrile, acetone, dimethyl sulfoxide or N, N-dimethylformamide, dichloromethane and trichloromethane.
Further, the organic base is triethylamine, triethylene diamine, diisopropylethylamine, pyridine or 1, 8-diazabicycloundecan-7-ene.
The oxalyl sulfonyl hydrazide prepared by the invention is used for olefin sulphonation reaction, substituted olefin and oxalyl sulfonyl hydrazide are used as raw materials, oxygen in air is used as an oxidant, and beta-keto sulfone or beta-hydroxy sulfone is generated through oxidation addition reaction in the presence of a catalyst, and the reaction formula is as follows:
wherein R is1，R2，R3，R4，R5Are each a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group.
The oxygen is used by exposing the reaction vessel to normal atmospheric pressure, or by using an air balloon, an air cylinder, an oxygen balloon or an oxygen cylinder.
The catalyst used in the reaction is copper iodide, cuprous iodide, copper acetate, ferric chloride, ferric bromide, cobalt chloride, ceric ammonium nitrate, iodine or tetrabutyl ammonium iodide; the solvent used in the reaction is one or more of water, ethanol, methanol, toluene, tetrahydrofuran, diethyl ether, dichloromethane, chloroform, acetonitrile, acetone, dimethyl sulfoxide or N, N-dimethylformamide.
The mass ratio of the substituted olefin to the oxalyl sulfonyl hydrazide is 1: 0.5-0.7; the amount ratio of the catalyst to the substituted olefin is 0.05 to 0.1: 1.
the invention has the beneficial effects that:
(1) the invention provides a preparation method of a sulfuryl reagent oxalyl sulfonyl hydrazide, which has the advantages of cheap raw materials, simple and convenient process and easy industrial preparation.
(2) The invention provides a novel method for preparing beta-keto sulfone or beta-hydroxy sulfone by using the oxalyl sulfonyl hydrazide as a sulfone-based reagent and reacting with olefin. The reaction takes air as an oxidant, is green, safe, efficient and environment-friendly, and is suitable for industrial production.
Detailed Description
Example one (preparation of oxalyl p-toluenesulfonyl hydrazide):
50ml of methylene chloride and 3.2 g (25mmol) of oxalyl chloride, which are solvents, were sequentially added to a 100ml reaction flask, and cooled to zero degrees in an ice bath, and then 9.3 g (50mmol) of p-toluenesulfonyl hydrazide and 5 g (50mmol) of triethylamine were sequentially added dropwise over a period of 10 minutes each. After the addition, the reaction was continued at zero degrees for 5 hours, and the aqueous layer was removed by extraction with water and ethyl acetate three times, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporator and purified by silica gel chromatography (methanol/dichloromethane ═ 1/10) to give pure oxalyl-p-toluenesulfonyl hydrazide 8.8 g, 82% yield
Example two:
2ml of ethanol as a solvent, 0.26 g (0.6mmol) of oxalyl p-toluenesulfonyl hydrazide, 0.052 g (0.5mmol) of styrene, and 1.9 mg (0.01mmol) of cuprous iodide as a catalyst were sequentially added to a 10ml reaction tube, and the reaction was left to react under an open atmosphere at room temperature, followed until complete disappearance of oxalyl p-toluenesulfonyl hydrazide. After the reaction was completed, extraction was performed with water and ethyl acetate three times, the aqueous layer was removed, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporator and then chromatographed on silica gel (acetic acid)Ethyl ester/petroleum ether-1/10) to yield 0.114 g of pure 2-p-toluenesulfonylacetophenone in 84% yield.1H NMR(400MHz,CDCl3)δ7.97(d,J＝7.7Hz,2H),7.78(d,J＝8.1Hz,2H),7.64(t,J＝7.3Hz,1H),7.50(t,J＝7.6Hz,2H),7.35(d,J＝8.0Hz,2H),4.74(s,2H),2.46(s,3H).13C NMR(101MHz,CDCl3)δ188.15,145.36,135.82,134.31,129.84,129.34,128.84,128.62,63.61,21.70。
EXAMPLE III
In reaction example two, the reaction was carried out in the same manner as in example two except that 0.052 g (0.5mmol) of styrene was changed to 0.092 g (0.5mmol) of 1-bromo-4-vinylbenzene. 2-p-toluenesulfonyl-4' -bromoacetophenone, yield 85%.1H NMR(400MHz,CDCl3)δ8.02(t,J＝1.8Hz,1H),7.91(ddd,J＝7.8,1.6,1.0Hz,1H),7.80–7.71(m,3H),7.38(dd,J＝15.3,7.8Hz,3H),4.70(s,2H),2.47(s,3H).13C NMR(101MHz,CDCl3)δ186.69,144.92,137.41,132.04,130.34,128.55,127.98,123.18,63.98。
Example four
In reaction example two, the reaction was carried out in the same manner as in example two except that 0.052 g (0.5mmol) of styrene was changed to 0.092 g (0.5mmol) of 1-bromo-3-vinylbenzene. 2-p-toluenesulfonyl-3' -bromoacetophenone, yield 77%.1H NMR(400MHz,CDCl3)δ8.02(t,J＝1.6Hz,1H),7.91(d,J＝7.8Hz,1H),7.76(t,J＝6.9Hz,3H),7.38(dd,J＝15.3,7.8Hz,3H),4.70(s,2H),2.47(s,3H).13C NMR(101MHz,CDCl3)δ186.98,145.64,137.41,137.12,135.54,132.09,130.40,129.95,128.60,128.03,123.18,63.68,21.75。
EXAMPLE five
In reaction example two, the reaction was carried out in the same manner as in example two except that 0.052 g (0.5mmol) of styrene was changed to 0.06 g (0.5mmol) of α -methylstyrene. 2-phenyl-1-p-toluenesulfonyl-2-propanol, yield 82%.1H NMR(400MHz,CDCl3)δ7.50(d,J＝8.3Hz,2H),7.33–7.29(m,2H),7.24–7.14(m,5H),4.66(s,1H),3.67(dd,J＝45.6,14.6Hz,2H),2.40(s,3H),1.72(s,3H).13C NMR(101MHz,CDCl3)δ144.53,137.39,133.62,129.71,128.25,127.56,127.13,124.65,73.17,66.69,30.76,21.57。
Claims (4)
1. Reacting oxalyl sulfonyl hydrazide
The application of the substituted alkene and the oxalyl sulfonyl hydrazide in the olefin sulphonation reaction is characterized in that substituted alkene and the oxalyl sulfonyl hydrazide are used as raw materials, oxygen in the air is used as an oxidant, and the beta-keto sulfone or the beta-hydroxy sulfone is generated through oxidation addition reaction in the presence of a catalyst copper iodide or cuprous iodide, and the reaction formula is as follows:
wherein R is1，R2，R3，R4Each independently a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group; r is aryl, heteroaryl, aryl or heteroaryl with substituent groups; in the formula (4), R2Not equal to H.
2. The use according to claim 1, wherein the oxygen is used by exposing the reaction vessel to the atmosphere to expose the reaction system to normal atmospheric pressure, or by using an air balloon, an air cylinder, an oxygen balloon or an oxygen cylinder.
3. The use according to claim 1, characterized in that the solvent used in the reaction is one or more of water, ethanol, methanol, toluene, tetrahydrofuran, diethyl ether, dichloromethane, chloroform, acetonitrile, acetone, dimethyl sulfoxide or N, N-dimethylformamide.
4. Use according to claim 1, characterized in that the mass ratio between the substituted alkene and the oxalyl sulfonyl hydrazide is 1:0.5 to 0.7; the amount ratio of the catalyst to the substituted olefin is 0.05 to 0.1: 1.
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