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 pho...

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Veröffentlicht in:Synthesis (Stuttgart) 2022-11, Vol.55 (9), p.1367-1374
Hauptverfasser: Murakami, Sho, Brudy, Cosima, Bachmann, Moritz, Takemoto, Yoshiji, Pieber, Bartholomäus
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Sprache:eng
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Zusammenfassung: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1979-5933