Abstract

In the past decades, borylation reactions have received extensive research interest and have developed into effective tools in the synthesis of versatile organoboron compounds. Boranes and symmetrical diboron compounds are commonly utilized as borylating reagents in these transformations, especially in the borylation reactions of unsaturated bonds. More recently, several types of unsymmetrical diboron reagents have been synthesized and applied in these borylation reactions, allowing for complementary chemo- and regioselectivity. This review aimed to highlight the recent development in this rising research field, focusing on new reactivity and selectivity that originates from the use of these unsymmetrical diboron reagents.

Highlights

  • Organoboron compounds, especially boronic acids and their derivatives, have served as the preeminent practical building blocks for the construction of molecular complexity and diversity for decades [1]

  • It has been well documented that they can be used as essential carbon nucleophiles in many types of transformations to introduce functional groups

  • In addition to various reactions that build up carbon-carbon bonds (e.g., Suzuki–Miyaura coupling) [2], a variety of carbon-heteroatom bonds can be constructed through the transformation of organoboron compounds [3,4]

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Summary

Introduction

Organoboron compounds, especially boronic acids and their derivatives, have served as the preeminent practical building blocks for the construction of molecular complexity and diversity for decades [1]. Such transformations been explored a long time since it is a research boron interestatoms of 3 hybridized diboron), was developedhave by Santos et al [22],for which contained mixed sp2 -sp main group chemistry, and the crucial conversion in the activation of various sp2-sp borylating and a lengthened, active B–B bond Such a structure removes the requirement for an external base in reagents [20,21]. In 2009, a preactivated sp2-sp diboron reagent, pinacolato diisopropanolaminato diboron (PDIPA diboron), was developed by Santos et al [22], which contained mixed sp2-sp hybridized boron atoms and a lengthened, active B–B bond Such a structure removes the requirement for an external base in the boryl transfer process. These transformations will be discussed according to the specific types of reactions below

Addition Reactions
LiOH-catalyzed
Addition
14. Cu-catalyzed
Other Types of Addition Reactions
17. Cu-catalyzed
Conclusions
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