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Synthesis 2023; 55(09): 1367-1374
DOI: 10.1055/a-1979-5933
DOI: 10.1055/a-1979-5933
special topic
Bürgenstock Special Section 2022 – Future Stars in Organic Chemistry
Photocatalytic Cleavage of Trityl Protected Thiols and Alcohols
We gratefully acknowledge the Max-Planck Society for generous financial support. S.M. acknowledges a Grant-in-Aid for Japan Society for the Promotion of Science (JSPS) Fellows and the Japan Society for the Promotion of Science (JSPS) for funding through the Overseas Challenge Program for Young Researchers. B.P. thanks the Boehringer Ingelheim Foundation for funding through the Plus 3 Perspectives Programme.
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 cleavageSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1979-5933.
- Supporting Information
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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