Issue 10, 2021
From the journal:

Chemical Science

Rhodium-catalysed selective C–C bond activation and borylation of cyclopropanes†

Yandong Wang,‡a   Jingyi Bai,‡a   Youqing Yang,‡a   Wenxuan Zhao,a   Yong Liang, ORCID logo *a   Di Wang,a   Yue Zhao ORCID logo a  and  Zhuangzhi Shi ORCID logo *a  

* Corresponding authors

a State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
E-mail: shiz@nju.edu.cn, yongliang@nju.edu.cn

Abstract

Transition metal (TM)-catalysed directed hydroboration of aliphatic internal olefins which facilitates the construction of complex alkylboronates is an essential synthetic methodology. Here, an efficient method for the borylation of cyclopropanes involving TM-catalysed directed C–C activation has been developed. Upon exposure to neutral Rh(I)-catalyst systems, N-Piv-substituted cyclopropylamines (CPAs) undergo proximal-selective hydroboration with HBpin to provide valuable γ-amino boronates in one step which are otherwise difficult to synthesize by known methods. The enantioenriched substrates can deliver chiral products without erosion of the enantioselectivities. Versatile synthetic utility of the obtained γ-amino boronates is also demonstrated. Experimental and computational mechanistic studies showed the preferred pathway and the origin of this selectivity. This study will enable the further use of CPAs as valuable building blocks for the tunable generation of C–heteroatom or C–C bonds through selective C–C bond activation.

Graphical abstract: Rhodium-catalysed selective C–C bond activation and borylation of cyclopropanes

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Article information

DOI
https://doi.org/10.1039/D0SC06186G
Article type
Edge Article
Submitted
10 Nov 2020
Accepted
14 Jan 2021
First published
15 Jan 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 3599-3607

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Rhodium-catalysed selective C–C bond activation and borylation of cyclopropanes

Y. Wang, J. Bai, Y. Yang, W. Zhao, Y. Liang, D. Wang, Y. Zhao and Z. Shi, Chem. Sci., 2021, 12, 3599 DOI: 10.1039/D0SC06186G

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