Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane

Livesley, Sarah, Trueman, Bethany, Robertson, Craig M ORCID: 0000-0002-4789-7607, Goundry, William RF, Morris, James A and Aissa, Christophe ORCID: 0000-0003-0750-9435 (2022) Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane. ORGANIC LETTERS, 24 (38). pp. 7015-7020.

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Official URL: http://dx.doi.org/10.1021/acs.orglett.2c02875

Abstract

Thiols easily react with [1.1.1]propellane to give sulfur-substituted bicyclo[1.1.1]pentanes in radical reactions, but this reactivity is not replicated in the case of heterocyclic thiols. Herein, we address this issue by electrophilically activating [1.1.1]propellane to promote its iodo-sulfenylation with 10 classes of heterocyclic thiols in two protocols that can be conducted on a multigram scale without exclusion of air or moisture.

Item Type:	Article
Depositing User:	Symplectic Admin
Date Deposited:	04 Oct 2022 07:01
Last Modified:	26 Jan 2023 00:16
DOI:	10.1021/acs.orglett.2c02875
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3165105