Angewandte Chemie - International Edition p. 9805 - 9809 (2018)
Update date:2022-08-04
Topics:
Yu, Wanwan
Hjerrild, Per
Jacobsen, Kristian M.
Tobiesen, Henriette N.
Clemmensen, Line
Poulsen, Thomas B.
The preparation of heteroatom-substituted p-quinones is ideally performed by direct addition of a nucleophile followed by in situ reoxidation. Albeit an appealing strategy, the reactivity of the p-quinone moiety is not easily tamed and no broadly applicable method for heteroatom functionalization exists. Shown herein is that Co(OAc)2 and Mn(OAc)3?2 H2O act as powerful catalysts for oxidative p-quinone functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine-26 is presented.
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