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Synthesis of gem-diboromethyl substituted bicyclo[1.1.1]pentanes and their application in palladium-catalysed cross couplings

01 November 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We describe a general transition-metal free synthesis of gem-diboromethyl substituted bicyclo[1.1.1]pentane (BCP) and other related C(sp3)-rich carbocyclic benzene bioisosteres from their corresponding p-tosylhydrazones. These novel functionalized benzene bioisosteres demonstrated unique reactivities towards palladium-catalyzed C(sp2)-C(sp3) cross couplings. The overall transformation can be applied to relatively complex substrates with potential utility in drug discovery.

Keywords

Bicyclo[1.1.1]pentane
Bioisostere
Hydrazone
Cross coupling

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Version History

Nov 01, 2022 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-96vc8
D O I: 10.26434/chemrxiv-2022-96vc8 [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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