Pushing the Ir-Catalyzed C-H Polyborylation of Aromatic Compounds to Maximum Capacity by Exploiting Reversibility

被引：131

作者：

Eliseeva, Maria N. ^{[1
]}

Scott, Lawrence T. ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 37期

基金：

美国国家科学基金会;

关键词：

COUPLING REACTIONS; DIRECT BORYLATION; PI-SYSTEMS; ONE-POT; ARENES; DERIVATIVES; ACTIVATION; FUNCTIONALIZATION; CONSTRUCTION; HETEROARENES;

D O I：

10.1021/ja307547j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Small amounts of base (e.g.,.10% potassium t-butoxide or sodium methoxide) have been found to promote equilibration of the kinetically favored products from Ir-catalyzed C-H polyborylations of aromatic compounds. In the presence of excess borylating agent, bis(pinacolato)diborane (B(2)pin(2)), repetitive deborylation/reborylations reposition the Bpin substituents until a pattern that accommodates the maximum number of Bpin substituents is achieved. A high-yield, one-step synthesis of 1,3,5,7,9-pentakis(Bpin)corannulene is reported that illustrates this useful extension of the Ir-catalyzed borylation reaction.

引用

页码：15169 / 15172

页数：4

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