Reductive stereo- and regiocontrolled boryllithiation and borylsodiation of arylacetylenes using flow microreactors

Author:

Jiang YiyuanORCID,Kurogi TakashiORCID,Yorimitsu HidekiORCID

Abstract

AbstractGiven their prevalence within valuable organic compounds, constructing multisubstituted alkenes while stereo- and regiochemically controlling the substituents on the alkene stands as a pivotal objective in organic synthesis. Now, the stereo- and regioselective syn-boryllithiation and syn-borylsodiation of arylacetylenes have been achieved by reductive borylmetallation using flow microreactors. This method involves the fast mixing of a solution of an alkyne and stoichiometric alkoxypinacolborane with an alkali metal arenide solution, which efficiently generates highly reactive β-borylalkenyllithium and β-borylalkenylsodium species by suppressing the undesired diboration that inevitably occurs in a batch reactor. Unlike conventional three-component borofunctionalization, the intermediates can be generated in the absence of electrophiles, which has enabled diverse electrophiles to participate in various syn-borofunctionalizations such as borylsilylation, borylhalogenation, borylcarbonylation, borylsulfenylation and borylarylation. Trapping with aldehydes and ketones provides a series of oxaboroles of biological interest. Furthermore, unsymmetric diarylacetylenes undergo highly regioselective borylmetallation, which is applicable to the stereo- and regiocontrolled syntheses of multisubstituted oxaboroles and differently tetrasubstituted alkenes.

Funder

MEXT | JST | Core Research for Evolutional Science and Technology

MEXT | Japan Society for the Promotion of Science

MEXT | Japan Science and Technology Agency

Publisher

Springer Science and Business Media LLC

Cited by 1 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Borylmetallation of alkynes made easy in flow;Nature Synthesis;2024-01-02

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