Photocatalytic Cleavage of Trityl Protected Thiols and Alcohols

Sho Murakami; Cosima Brudy; Moritz Bachmann; Yoshiji Takemoto; Bartholomäus Pieber

doi:10.1055/a-1979-5933

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(09): 1367-1374
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‡

^aDepartment of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany

^bGraduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan

,

Cosima Brudy‡

^aDepartment of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany

,

Moritz Bachmann

^aDepartment of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany

,

Yoshiji Takemoto

^bGraduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan

,

Bartholomäus Pieber ∗

^aDepartment of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany

› Institutsangaben

Abstract

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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

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Referenzen

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