Pd-Carbene Migratory Insertion: Application to the Synthesis of Trifluoromethylated Alkenes and Dienes

被引：74

作者：

Wang, Xi ^{[1
,2
]}

Xu, Yan ^{[1
,2
]}

Deng, Yifan ^{[1
,2
]}

Zhou, Yujing ^{[1
,2
]}

Feng, Jiajie ^{[1
,2
]}

Ji, Guojing ^{[1
,2
]}

Zhang, Yan ^{[1
,2
]}

Wang, Jianbo ^{[1
,2
,3
]}

机构：

[1] Peking Univ, Minist Educ, Coll Chem, BNLMS, Beijing 100871, Peoples R China

[2] Peking Univ, Minist Educ, Coll Chem, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 04期

关键词：

alkene synthesis; cross-coupling reactions; diazo compounds; palladium; trifluoromethylation; SILVER-MEDIATED TRIFLUOROMETHYLATION; ONE-CARBON UNITS; PALLADIUM-CATALYZED TRIFLUOROMETHYLATION; NUCLEOPHILIC 5-ENDO-TRIG CYCLIZATION; ALPHA-TRIFLUOROMETHYLSTYRENES; GEM-DIFLUOROALKENES; FLUORINE; DERIVATIVES; EFFICIENT; REAGENTS;

D O I：

10.1002/chem.201304143

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pd-catalyzed cross-coupling of halides with CF3-substituted diazo compounds or N-tosylhydrazones has been explored for the synthesis of CF3-substituted alkenes and 1,3-butadienes. Pd-carbene migratory insertion plays the key role in these transformations.

引用

页码：961 / 965

页数：5

共 95 条

[1]

[Anonymous], 2012, ANGEW CHEM

[2]

[Anonymous], 2011, Angew. Chem.

[3]

[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANGE.201107414

[4] Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].

Barluenga, Jose ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500

[5] Addition of organolithium reagents to alpha-(trifluoromethyl)styrene: Concise synthesis of functionalised gem-difluoroalkenes [J].

Begue, JP ;

BonnetDelpon, D ;

Rock, MH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (12) :1409-1413

[6]

Besset T., 2012, ANGEW CHEM, V124, P5134

[7] Tamed Arene and Heteroarene Trifluoromethylation [J].

Besset, Tatiana ;

Schneider, Cedric ;

Cahard, Dominique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050

[8] Trifluoromethylalkenes in cycloaddition reactions [J].

BonnetDelpon, D ;

Begue, JP ;

Lequeux, T ;

Ourevitch, M .

TETRAHEDRON, 1996, 52 (01) :59-70

[9] The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates [J].

Cho, Eun Jin ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2011, 13 (24) :6552-6555

[10] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].

Cho, Eun Jin ;

Senecal, Todd D. ;

Kinzel, Tom ;

Zhang, Yong ;

Watson, Donald A. ;

Buchwald, Stephen L. .

SCIENCE, 2010, 328 (5986) :1679-1681

← 1 2 3 4 5 6 7 8 9 10 →