Catalyst-Controlled 1,2-and 1,1-Arylboration of -Alkyl Alkenyl Arenes

被引：82

作者：

Bergmann, Allison M. ^{[1
]}

Dorn, Stanna K. ^{[1
]}

Smith, Kevin B. ^{[1
]}

Logan, Kaitlyn M. ^{[1
]}

Brown, M. Kevin ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, 800 E Kirkwood Ave, Bloomington, IN 47405 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 06期

关键词：

carboboration; copper; cross-coupling; homogeneous catalysis; palladium; CROSS-COUPLING REACTIONS; ENANTIOSELECTIVE ARYLBORATION; REGIOSELECTIVE ARYLBORATION; ARYL BROMIDES; TERTIARY; COPPER; COMPLEXES; REAGENTS; 1,1-DIARYLATION; SECONDARY;

D O I：

10.1002/anie.201812533

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two methods are reported for the 1,2- and 1,1-arylboration of -methyl vinyl arenes. In the case of 1,2-arylboration, the formation of a quaternary center occurred through a rare cross-coupling reaction of a tertiary organometallic complex. 1,1-Arylboration was enabled by catalyst optimization and occurred through a -hydride elimination/reinsertion cascade. Enantioselective variants of both processes are presented as well as mechanistic investigations.

引用

页码：1719 / 1723

页数：5

共 61 条

[41]

Ren P., 2012, Angew. Chem, V124, P9244

[42] Copper-Catalyzed Cross-Coupling of Functionalized Alkyl Halides and Tosylates with Secondary and Tertiary Alkyl Grignard Reagents [J].

Ren, Peng ;

Stern, Lucas-Alexandre ;

Hu, Xile .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :9110-9113

[43] Pd(0)-Catalyzed 1,1-Diarylation of Ethylene and Allylic Carbonates [J].

Saini, Vaneet ;

Liao, Longyan ;

Wang, Qiaofeng ;

Jana, Ranjan ;

Sigman, Matthew S. .

ORGANIC LETTERS, 2013, 15 (19) :5008-5011

[44] Palladium-Catalyzed 1,1-Difunctionalization of Ethylene [J].

Saini, Vaneet ;

Sigman, Matthew S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (28) :11372-11375

[45] Catalyst Controlled Regiodivergent Arylboration of Dienes [J].

Sardini, Stephen R. ;

Brown, M. Kevin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (29) :9823-9826

[46] Arylboration of 1-Arylalkenes by Cooperative Nickel/Copper Catalysis [J].

Semba, Kazuhiko ;

Ohtagaki, Yasuhiro ;

Nakao, Yoshiaki .

ORGANIC LETTERS, 2016, 18 (16) :3956-3959

[47] Copper-catalyzed borylative transformations of non-polar carbon-carbon unsaturated compounds employing borylcopper as an active catalyst species [J].

Semba, Kazuhiko ;

Fujihara, Tetsuaki ;

Terao, Jun ;

Tsuji, Yasushi .

TETRAHEDRON, 2015, 71 (15) :2183-2197

[48] Arylboration of Alkenes by Cooperative Palladium/Copper Catalysis [J].

Semba, Kazuhiko ;

Nakao, Yoshiaki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (21) :7567-7570

[49] Copper- and Nickel-Catalyzed Cross-Coupling Reaction of Monofluoroalkenes with Tertiary, Secondary, and Primary Alkyl and Aryl Grignard Reagents [J].

Shi, Hongyan ;

Dai, Wenpeng ;

Wang, Biyun ;

Cao, Song .

ORGANOMETALLICS, 2018, 37 (03) :459-463

[50] Recent progress in copper-catalyzed difunctionalization of unactivated carbon-carbon multiple bonds [J].

Shimizu, Yohei ;

Kanai, Motomu .

TETRAHEDRON LETTERS, 2014, 55 (28) :3727-3737

← 1 2 3 4 5 6 7 →