Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes

Dedicated to Professor Zuowei Xie on the occasion of his 60^th birthday

Abstract

1,1-Diborylalkene, a class of important diboryl species, serves as the synthetic precursor of multisubstituted olefin, which is a prevalent building block in natural products, functional materials, and pharmaceuticals. Current methods mainly afford symmetrical 1,1-diborylalkenes, and late-stage differentiation of the two identical boryl groups is required to achieve selective difunctionalization. In comparison, stereoselective synthesis of unsymmetrical 1,1-diborylalkenes (UDBA) are less-explored. This Synpacts article provides a brief summary of the achievements in the synthesis of UDBAs. In particularly, we highlight our recent work on the unsymmetrical 1,1-diborylation of alkynes using a neutral sp²–sp³ diboron reagent to access UDBAs and their controllable stepwise derivatization.

1 Introduction

2 Background: Unsymmetrical 1,1-Diborylalkene Synthesis

3 Stereoselective Unsymmetrical 1,1-Diborylation of Alkynes with a Neutral sp²–sp³ Diboron Reagent

4 Summary and Outlook

Key words

boron - unsymmetrical 1,1-diborylalkene - diborylation - diboron reagent - stereoselective

Publication History

Received: 28 December 2023

Accepted after revision: 18 March 2024

Article published online:
02 April 2024

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