Difluoromethyl phenyl sulfone, a difluoromethylidene equivalent: Use in the synthesis of 1,1-difluoro-1-alkenes

被引：72

作者：

Prakash, GKS

Hu, JB

Ying, W

Olah, GA

机构：

[1] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA

[2] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 39期

关键词：

alkenes; fluorination; elimination; fluorine; nucleophilic substitution;

D O I：

10.1002/anie.200460815

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A nucleophilic substitution-elimination reaction strategy in which difluoromethyl phenyl sulfone is used as a selective difluoromethylidene equivalent allows the facile synthesis of 1,1-difluoro-1-alkenes from primary alkyl halides (see scheme).

引用

页码：5203 / 5206

页数：4

共 45 条

[31] Preparation of tri- and difluoromethylsilanes via an unusual magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes using tri- and difluoromethyl sulfides, sulfoxides, and sulfones [J].

Prakash, GKS ;

Hu, JB ;

Olah, GA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4457-4463

[32] Difluoromethyl phenyl sulfone as a selective difluoromethylene dianion equivalent:: One-pot stereoselective synthesis of anti-2,2-difluoropropane-1,3-diols [J].

Prakash, GKS ;

Hu, JB ;

Mathew, T ;

Olah, GA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (42) :5216-5219

[33]

PRAKASH GKS, 2003, ANGEW CHEM, V115, P5374

[34]

Sevenard DV, 2001, SYNLETT, P379

[35] REGIOSELECTIVITY IN THE ADDITION OF CARBON NUCLEOPHILES TO 1-FLUORO AND 1,1-DIFLUORO PI-ALLYLPALLADIUM COMPLEXES [J].

SHI, GQ ;

HUANG, XH ;

ZHANG, FJ .

TETRAHEDRON LETTERS, 1995, 36 (35) :6305-6308

[36] NUCLEOPHILIC-ADDITION OF DIFLUOROMETHYL PHENYL SULFONE TO ALDEHYDES AND VARIOUS TRANSFORMATIONS OF THE RESULTING ALCOHOLS [J].

STAHLY, GP .

JOURNAL OF FLUORINE CHEMISTRY, 1989, 43 (01) :53-66

[37]

Toyota A, 1996, CHEM PHARM BULL, V44, P703

[38] Methods for the synthesis of gem-difluoromethylene compounds [J].

Tozer, MJ ;

Herpin, TF .

TETRAHEDRON, 1996, 52 (26) :8619-8683

[39] SULFONES AS CHEMICAL CHAMELEONS - CYCLIZATION VIA 1,1-DIPOLE SYNTHONS [J].

TROST, BM ;

GHADIRI, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (23) :7260-7261

[40] CHEMICAL CHAMELEONS - ORGANOSULFONES AS SYNTHETIC BUILDING-BLOCKS [J].

TROST, BM .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (01) :107-124

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