Directing-Group-Assisted Transition-Metal-Catalyzed Selective BH Functionalization of o-Carboranes

Author:

Xie Zuowei1,Zhang Jie2

Affiliation:

1. Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology

2. Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong Shatin NT

Abstract

AbstractCarboranes are a type of molecular clusters consisting of carbon, hydrogen, and boron atoms. They possess unique characteristics, such as three-dimensional aromaticity, icosahedral geometry, and robustness. Functionalized carboranes have been utilized in various fields, including medicine, materials, and organometallic/coordination chemistry. In this context, selective functionalization of o-carboranes has received tremendous attention, specifically in the regio- and enantioselective modification of the ten chemically similar BH vertices within the carborane cage. In recent years, significant progress has been made in catalytic vertex-specific BH functionalization, as well as achieving enantioselective functionalization of the cage BH. This review provides an overview of the recent advancements in this research field.1 Introduction2 Carboxy-Assisted BH Functionalization2.1 Formation of B–C Bonds2.2 Formation of B–N Bonds2.3 Formation of B–O Bonds2.4 Formation of B–X Bonds2.5 Consecutive Formation of B–C and B–Y (Y = N, O) Bonds3 N-Based Directing-Group-Assisted B–H Functionalization3.1 Acylamino as a Directing Group3.2 Amide as a Directing Group3.3 Pyridyl as a Directing Group3.4 Imine as a Directing Group4 Phosphinyl-Assisted Cage B–H Functionalization5 Bidentate-Directing-Group-Assisted B–H Functionalization6 Other Directing-Group-Assisted B–H Functionalization7 Conclusions

Funder

Research Grants Council, University Grants Committee

Shenzhen Science and Technology Innovation Program

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

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