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Construction of Axially Chiral Arylborons via Atroposelective Miyaura Borylation

Kai Yang, Yanfei Mao, Jie Xu, Hao Wang, Yong He, Wangyang Li, Qiuling Song

2021Journal of the American Chemical Society91 citationsDOI

Abstract

Compared with the well-developed centrally chiral boron chemistry, C-B axially chiral chemistry remains elusive and challenging. Herein we report the first atroposelective Miyaura borylation of bromoarenes with unsymmetrical diboron reagents for the direct catalytic synthesis of optically active atropisomeric arylborons. This reaction features broad substrate scope and produces axially chiral arylborons with high yields and good enantioselectivities.

Topics & Concepts

ChemistryBorylationAxial symmetryReagentBoronCombinatorial chemistryOptically activeSubstrate (aquarium)CatalysisScope (computer science)Organic chemistryComputational chemistryArylEngineeringStructural engineeringOceanographyAlkylComputer scienceProgramming languageGeologyAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAlkaloids: synthesis and pharmacology
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