Synthesis 2020; 52(05): 629-644
DOI: 10.1055/s-0039-1690762
review
© Georg Thieme Verlag Stuttgart · New York

Organo-f-Complexes for Efficient and Selective Hydroborations

Heng Liu
a  Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa City 32000, Israel   Email: chmoris@technion.ac.il
b  CAS Key Laboratory of High-Performance Synthetic Rubber and Its Composite Materials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, 130022, Jilin, P. R. of China   Email: hengliu@ciac.ac.cn
,
a  Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa City 32000, Israel   Email: chmoris@technion.ac.il
› Author Affiliations
This work was supported by the Israel Science Foundation administered by the Israel Academy of Science and Humanities under Contract No. 184/18.
Further Information

Publication History

Received: 17 November 2019

Accepted: 18 November 2019

Publication Date:
02 January 2020 (online)


Abstract

Organo-f-complexes catalyzing small molecule transformations have been a hot topic in the past few years. Compared to other transformations, the hydroboration of C=X (X = C, N, O) unsaturated bonds serves as an important strategy to prepare organoborane derivatives, which are important intermediates in organic synthesis. This review outlines recent advances in organolanthanide and organoactinide complexes promoting the hydroboration of C=X containing substrates. After a brief introduction, three types of hydroboration will be presented: alkene hydroboration, carbonyl hydroboration, and imine and nitrile hydroborations. The catalytic performance, mechanism, and kinetic studies are discussed in detail, aiming to emphasize the catalytic differences between the diverse organo-f-catalysts. Additionally, challenges and future directions of this field are also presented.

1 Introduction

2 Alkene Hydroboration

3 Carbonyl Hydroboration

4 Imine and Nitrile Hydroboration

5 Conclusions and Outlook

 
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