Premium
Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene–Rhodium Complex: Direct Access to cis ‐Substituted Borylated Cycloalkanes and Saturated Heterocycles
Author(s) -
Ling Liang,
He Yuan,
Zhang Xue,
Luo Meiming,
Zeng Xiaoming
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201811210
Subject(s) - carbene , chemistry , alkyl , aryl , rhodium , reactivity (psychology) , stereoselectivity , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , medicine , alternative medicine , pathology
Abstract We herein report the hydrogenation of substituted aryl‐ and heteroaryl boronate esters for the selective synthesis of cis‐substituted borylated cycloalkanes and saturated heterocycles. A cyclic (alkyl)(amino)carbene‐ligated rhodium complex with two dimethyl groups at the ortho‐alkyl scaffold of the carbene showed high reactivity in promoting the hydrogenation, thereby enabling the hydrogenation of (hetero)arenes with retention of the synthetically valuable boronate group. This process constitutes a clean, atom‐economic, as well as chemo‐ and stereoselective route for the generation of cis‐configured, diversely substituted borylated cycloalkanes and saturated heterocycles that are usually elusive and difficult to prepare.