A NOVEL SYNTHESIS OF DISUBSTITUTED 1,1-DIFLUORO-1-ALKENES BY USING 2,2,2-TRIFLUOROETHYL PARA-TOLUENESULFONATE AS A DIFLUOROVINYLIDENE UNIT

被引：32

作者：

ICHIKAWA, J ^{[1
]}

MORIYA, T ^{[1
]}

SONODA, T ^{[1
]}

KOBAYASHI, H ^{[1
]}

机构：

[1] KYUSHU UNIV, GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN

来源：

CHEMISTRY LETTERS | 1991年 / 06期

关键词：

D O I：

10.1246/cl.1991.961

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2,2,2-Trifluoroethyl p-toluenesulfonate is treated with lithium diisopropylamide and trialkylboranes successively to generate 1-alkyl-2,2-difluorovinylboranes, which in turn couple with aryl iodides in the presence of palladium catalyst and tetrabutylammonium fluoride to afford disubstituted 1,1-difluoro-1-alkenes in good yields.

引用

页码：961 / 964

页数：4

共 21 条

[1] METAL DEHALOGENATION ROUTE TO REACTIVE FLUORO-OLEFINS [J].

BURTON, DJ ;

KESLING, HS ;

NAAE, DG .

JOURNAL OF FLUORINE CHEMISTRY, 1981, 18 (03) :293-298

[2]

CHAMBERS RD, 1965, ADV FLUORINE CHEM, V4, P50

[3]

CHAMBERS RD, 1979, COMPREHENSIVE ORGANI, V1, P545

[4] A WIDE-RANGE OF ORGANOSILICON COMPOUNDS COUPLES WITH ENOL AND ARYL TRIFLATES IN THE PRESENCE OF PD CATALYST AND FLUORIDE-ION [J].

HATANAKA, Y ;

HIYAMA, T .

TETRAHEDRON LETTERS, 1990, 31 (19) :2719-2722

[5]

HUDLICKY M, 1976, CHEM ORGANIC FLUORIN, pCH5

[6] A NOVEL SYNTHESIS OF 1,1-DIFLUOROOLEFINS FROM 1,1,1-TRIFLUOROETHYL P-TOLUENESULFONATE VIA BORON ATE-COMPLEX [J].

ICHIKAWA, J ;

SONODA, T ;

KOBAYASHI, H .

TETRAHEDRON LETTERS, 1989, 30 (13) :1641-1644

[7] REACTIONS OF 2,2-DIFLUOROALKENYLBORANES WITH HALOGENS IN THE PRESENCE OF BASE - NOVEL SYNTHESES OF SYMMETRICALLY DISUBSTITUTED 1,1-DIFLUORO-1-ALKENES AND 1,1-DIFLUORO-2-IODO-1-ALKENES [J].

ICHIKAWA, J ;

SONODA, T ;

KOBAYASHI, H .

TETRAHEDRON LETTERS, 1989, 30 (46) :6379-6382

[8] ORGANOCUPRATE-INDUCED SUBSTITUTION OF THE ENOL OXYGEN MOIETY IN 2,2-DIFLUORO ENOL PHOSPHATES WITH ALLYL HALIDES - A NOVEL ROUTE TO GEM-DIFLUOROOLEFINS FROM CHLORODIFLUOROMETHYL KETONES [J].

ISHIHARA, T ;

YAMANA, M ;

ANDO, T .

TETRAHEDRON LETTERS, 1983, 24 (50) :5657-5660

[9] STEREOSPECIFIC AND REGIOSPECIFIC SYNTHESES TO PROVIDE CONJUGATED (E,Z)-ALKADIENES AND (Z,Z)-ALKADIENES, AND ARYLATED (Z)-ALKENES IN EXCELLENT YIELDS VIA THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF (Z)-1-ALKENYLBORONATES WITH 1-BROMOALKENES AND ARYL IODIDES [J].

MIYAURA, N ;

SATOH, M ;

SUZUKI, A .

TETRAHEDRON LETTERS, 1986, 27 (32) :3745-3748

[10] STEREOSELECTIVE SYNTHESIS OF ARYLATED (E)-ALKENES BY THE REACTION OF ALK-1-ENYLBORANES WITH ARYL HALIDES IN THE PRESENCE OF PALLADIUM CATALYST [J].

MIYAURA, N ;

SUZUKI, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (19) :866-867

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