Water-assisted diboron activation: efficient synthesis of alkyl 1,2-bis(boronates) and 1,1,2-tris(boronates)†

IF 9.2 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Green Chemistry Pub Date : 2025-05-07 DOI:10.1039/d5gc00743g

Kiran S. Patil , Shivakumar Reddappa , Maruti Suryavansi , Srinivasa Budagumpi , D. H. Nagaraju , Manoj V. Mane , Shubhankar Kumar Bose

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引用次数: 0

Abstract

Multifunctionalization of easily accessible feedstocks namely alkenes and alkynes to synthesize polyboronate compounds represents an extremely useful process in organic synthesis. Herein, we disclose a method to access synthetically versatile alkyl 1,2-bis(boronates) and 1,1,2-tris(boronates) via metal- and base-free diboration and triboration of alkenes and alkynes, respectively, with bis(pinacolato)diboron (B₂pin₂) as the boron reagent, aided by water, which is yet unknown. This strategy's practicality and industrial importance are demonstrated by avoiding the use of stoichiometric amounts of base and its operational simplicity. This protocol demonstrates broad substrate scope and good functional-group tolerance on alkenes and alkynes. Preliminary mechanistic studies reveal the formation of tetrahydroxydiboron as an active boron reagent for these C–B bond formation reactions. The most striking feature of this procedure is the synthesis of multiboronate compounds without using any organic solvents and facile extractive workup.

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水辅助二硼活化：高效合成烷基1,2-二（硼酸盐）和1,1,2-三（硼酸盐）†

在有机合成中，容易获得的原料即烯烃和炔的多功能化合成聚硼酸盐化合物是一个非常有用的过程。在此，我们公开了一种合成多用途烷基1,2-双（硼酸盐）和1,1,2-三（硼酸盐）的方法，分别通过烯烃和炔烃的无金属和无碱双硼酸盐和三硼酸盐，以双（pinacolato）二硼（B2pin2）作为硼试剂，在水的辅助下，尚不清楚。通过避免使用化学计量量的碱及其操作的简单性，证明了该策略的实用性和工业重要性。该方案显示出广泛的底物范围和良好的官能团对烯烃和炔烃的耐受性。初步的机理研究揭示了四羟基二硼的形成作为这些C-B键形成反应的活性硼试剂。这个过程最显著的特点是合成多硼化合物不使用任何有机溶剂和易于提取的工作。

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来源期刊

Green Chemistry 化学-化学综合

CiteScore

16.10

自引率

7.10%

发文量

677

审稿时长

1.4 months

期刊介绍： Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.