Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide

被引：77

作者：

Liu, Jiandong ^{[1
]}

Gong, Hegui ^{[1
]}

Zhu, Shaolin ^{[2
]}

机构：

[1] Shanghai Univ, Sch Mat Sci & Engn, Ctr Supramol Chem & Catalysis, Dept Chem, Shanghai 200444, Peoples R China

[2] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Jiangsu Key Lab Adv Organ Mat Chem & Biomed, Nanjing 210093, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 08期

关键词：

alkenes; alkenylation; asymmetric catalysis; isomerization; nickel; LINEAR-SELECTIVE HYDROARYLATION; SECONDARY ALKYL ELECTROPHILES; COUPLING REACTIONS; CROSS-COUPLINGS; ISOMERIZATION-HYDROBORATION; REMOTE; HALIDES; FUNCTIONALIZATION; ARYLATION; VINYL;

D O I：

10.1002/anie.202012614

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.

引用

页码：4060 / 4064

页数：5

共 50 条

[41] Nickel-Catalyzed Regio- and Stereoselective Reductive Coupling between Methylenecyclopropanes, Aldehydes, and Triethylborane with Retention of the Cyclopropane Ring [J].

Ogata, Kenichi ;

Shimada, Daisuke ;

Fukuzawa, Shin-ichi .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (20) :6142-6146

[42] Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling [J].

Tu, Hai-Yong ;

Wang, Fang ;

Huo, Liping ;

Li, Yuanbo ;

Zhu, Shengqing ;

Zhao, Xian ;

Li, Huan ;

Qing, Feng-Ling ;

Chu, Lingling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (21) :9604-9611

[43] Nickel-catalyzed dynamic kinetic cross-electrophile coupling of benzylic alcohols and alkenyl triflates [J].

Peng, Xuejing ;

Huang, Jingxian ;

Han, Guan-Yu ;

Shu, Xing-Zhong .

ORGANIC CHEMISTRY FRONTIERS, 2023, 11 (01) :94-99

[44] Nickel-catalyzed regio- and stereo-selective synthesis of homoallylic alcohol derivatives from dienes and aldehydes [J].

Takimoto, M ;

Hiraga, Y ;

Sato, Y ;

Mori, M .

TETRAHEDRON LETTERS, 1998, 39 (25) :4543-4546

[45] Enantioselective Synthesis of Benzylic Boronic Esters via Photoredox/Nickel-Catalyzed Multicomponent Cross-Couplings [J].

He, Xu ;

Shi, Enxue ;

Xiao, Junhua .

ORGANIC LETTERS, 2024, 26 (45) :9728-9734

[46] Highly Regio- and Enantioselective Copper-Catalyzed Hydroboration of Styrenes [J].

Noh, Dongwan ;

Chea, Heesung ;

Ju, Junghwan ;

Yun, Jaesook .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6062-6064

[47] Nickel-Catalyzed Regio- and Enantioselective Annulation Reactions of 1,2,3,4-Benzothiatriazine-1,1(2H)-dioxides with Allenes [J].

Miura, Tomoya ;

Yamauchi, Motoshi ;

Kosaka, Akira ;

Murakami, Masahiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) :4955-4957

[48] Enantioselective Nickel-Catalyzed Domino and Tandem Processes [J].

Pellissier, Helene .

CURRENT ORGANIC CHEMISTRY, 2016, 20 (03) :234-265

[49] Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions [J].

Poremba, Kelsey E. ;

Dibrell, Sara E. ;

Reisman, Sarah E. .

ACS CATALYSIS, 2020, 10 (15) :8237-8246

[50] Nickel-catalyzed highly regio- and stereoselective cyclization of oxanorbornenes with alkyl propiolates: A novel method for the synthesis of benzocoumarin derivatives [J].

Rayabarapu, DK ;

Sambaiah, T ;

Cheng, CH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (07) :1286-+

← 1 2 3 4 5 →