Catalyst-Free Regioselective Diborylation of Aryllithium with Tetra(o-tolyl)diborane(4)

Mao，Xiaofeng1; Lu，Zhenpin2; Zhang，Jie1; Xie，Zuowei1,3

2024-02-05

10.1002/anie.202317614

Angewandte Chemie - International Edition   影响因子和分区

1433-7851

1521-3773

A catalyst-free 1,2-diborylation of aryllithium with tetra(o-tolyl)diborane(4) has been achieved, giving a series of 1,2-diborylaryl lithium species in excellent yields under mild reaction conditions, which leads to 1,2-di(tolyl)borylarenes in 60–91 % yields upon treatment with the hydride-abstracting reagent. In these transformations, one sp C−H of arene is activated and both boryl units are utilized to build two new (sp)C−B bonds. This represents a new strategy for selective arene diborylation. Density functional theory (DFT) calculations suggest that an aromatic nucleophilic substitution is a key step in the formation of the products.

Arene Boron Borylation Diborane Diborylation

SCI ; EI

英语

通讯

CHEMISTRY

2-s2.0-85181752094

Scopus

1.Department of Chemistry and State Key Laboratory of Synthetic Chemistry,The Chinese University of Hong Kong,Shatin,N. T.,Hong Kong
2.Department of Chemistry,City University of Hong Kong,Hong Kong
3.Shenzhen Grubbs Institute and Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China

Mao，Xiaofeng,Lu，Zhenpin,Zhang，Jie,et al. Catalyst-Free Regioselective Diborylation of Aryllithium with Tetra(o-tolyl)diborane(4)[J]. Angewandte Chemie - International Edition,2024,63(6).

Mao，Xiaofeng,Lu，Zhenpin,Zhang，Jie,&Xie，Zuowei.(2024).Catalyst-Free Regioselective Diborylation of Aryllithium with Tetra(o-tolyl)diborane(4).Angewandte Chemie - International Edition,63(6).

Mao，Xiaofeng,et al."Catalyst-Free Regioselective Diborylation of Aryllithium with Tetra(o-tolyl)diborane(4)".Angewandte Chemie - International Edition 63.6(2024).