Synthesis
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

Sho Murakami
a   Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany
b   Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
,
Cosima Brudy
a   Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany
,
Moritz Bachmann
a   Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany
,
Yoshiji Takemoto
b   Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
,
a   Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany
› Author Affiliations
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.

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

© 2022. Thieme. All rights reserved

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