Photocatalytic Cleavage of Trityl Protected Thiols and Alcohols

Abstract

We report the visible light photocatalytic cleavage of trityl thioethers or ethers under pH-neutral conditions. The method results in the formation of the respective symmetrical disulfides and alcohols in moderate to excellent yield. The protocol only requires the addition of a suitable photocatalyst and light rendering it orthogonal to several functionalities, including acid labile protective groups. The same conditions can be used to directly convert trityl-protected thiols into unsymmetrical disulfides or selenosulfides, and to cleave trityl resins in solid phase organic synthesis.

Key words

photocatalysis - protective group cleavage - detritylation - carbon–heteroatom bond cleavage - resin cleavage

Publication History

Received: 19 October 2022

Accepted after revision: 15 November 2022

Accepted Manuscript online:
15 November 2022

Article published online:
07 December 2022

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