Sulfoximine Assisted Pd(II)-Catalyzed Bromination and Chlorination of Primary β-C(sp3)-H Bond

被引：123

作者：

Rit, Raja K. ^{[1
]}

Yadav, M. Ramu ^{[1
]}

Ghosh, Koushik ^{[1
]}

Shankar, Majji ^{[1
]}

Sahoo, Akhila K. ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 20期

关键词：

C-H BONDS; REDUCTIVE ELIMINATION; C(SP(3))-H BONDS; HALOGENATION; HALIDES; MILD; BETA; IODINATION; ACTIVATION; COMPLEXES;

D O I：

10.1021/ol502337b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

S-Methyl-S-2-pyridyl-sulfoximine (MPyS) directed bromination and chlorination of the 1 degrees-beta-C(sp(3))-H bond of MPyS-N-amides is realized under the influence of N-Br/Cl-phthalimides and a Pd(II)-catalyst. The sequential halogenation and acetoxylation of alpha-dimethyl MPyS-N-amides constructs highly functionalized alpha-trisubstituted aliphatic acid derivatives. The MPyS directing group is cleaved from the halogenated products and recovered.

引用

页码：5258 / 5261

页数：4

共 55 条

[1] Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance [J].

Aihara, Yoshinori ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :898-901

[2] Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives [J].

Ano, Yusuke ;

Tobisu, Mamoru ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12984-12986

[3]

[Anonymous], 2007, ORGANIC REACTION MEC

[4]

[Anonymous], ORG LETT

[5]

[Anonymous], TOPICS IN ORGANOMETA

[6]

[Anonymous], ORG LETT

[7]

[Anonymous], 1996, HDB GRIGNARD REAGENT

[8]

[Anonymous], J AM CHEM SOC

[9] Mild C-H Halogenation of Anilides and the Isolation of an Unusual Palladium(I)-Palladium(II) Species [J].

Bedford, Robin B. ;

Haddow, Mairi F. ;

Mitchell, Charlotte J. ;

Webster, Ruth L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (24) :5524-5527

[10] DEVELOPMENT OF ORGANOPALLADIUM(IV) CHEMISTRY - FUNDAMENTAL-ASPECTS AND SYSTEMS FOR STUDIES OF MECHANISM IN ORGANOMETALLIC CHEMISTRY AND CATALYSIS [J].

CANTY, AJ .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (02) :83-90

← 1 2 3 4 5 6 →