C-N Bond Cleavage of Allylic Amines via Hydrogen Bond Activation with Alcohol Solvents in Pd-Catalyzed Allylic Alkylation of Carbonyl Compounds

被引：244

作者：

Zhao, Xiaohu ^{[1
]}

Liu, Delong ^{[2
]}

Guo, Hui ^{[2
]}

Liu, Yangang ^{[2
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai 200240, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 48期

关键词：

CHIRAL DIPHOSPHINE LIGANDS; COMPLEXES; SUBSTITUTIONS; ALLYLATION; CYCLOPROPANATION; ALLYLENAMINES; REARRANGEMENT; NUCLEOPHILES; DERIVATIVES; IMINES;

D O I：

10.1021/ja209373k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hydrogen-bond-activated C-N bond cleavage of allylic amines was realized in Pd-catalyzed allylic alkylation to form the C-C bond product. The method could be expanded to a series of allylic amines and carbonyl compounds with excellent results. It provides a new and convenient access to C-C bond formation based on Pd-catalyzed allylic alkylation of allylic amines by using only inexpensive alcohol solvents.

引用

页码：19354 / 19357

页数：4

共 58 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[2]

[Anonymous], 2004, METAL CATALYZED CROS

[3]

[Anonymous], 2003, Organic chemistry

[4] Catalytic Enantioselective [2,3]-Rearrangements of Amine N-Oxides [J].

Bao, Hongli ;

Qi, Xiangbing ;

Tambar, Uttam K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) :1206-1208

[5]

BELLER M, 2002, HDB ORGANOPALLADIUM, V1

[6] Tsuji-Trost allylic alkylation with ketone enolates [J].

Braun, Manfred ;

Meier, Thorsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) :6952-6955

[7] Phosphinite Thioethers Derived from Chiral Epoxides. Modular P,S-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions [J].

Caldentey, Xisco ;

Pericas, Miguel A. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08) :2628-2644

[8] Chemo- and Regioselectivity-Tunable Pd-Catalyzed Allylic Alkylation of Imines [J].

Chen, Jian-Ping ;

Peng, Qian ;

Lei, Bai-Lin ;

Hou, Xue-Long ;

Wu, Yun-Dong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (36) :14180-14183

[9]

Diederich F., 1998, Metal-Catalyzed Cross-Coupling Reactions

[10] Organosulfur compounds: Electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions [J].

Dubbaka, SR ;

Vogel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7674-7684

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