Unusual 1,2-aryl migration in Pd(ii)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines

Organic & Biomolecular Chemistry
So Won Youn, So Ra Lee

Abstract

Inspired by the Hegedus aza-Wacker indole synthesis, we were intrigued with the fate of the aminopalladation intermediate if syn β-hydrogen is made inaccessible or unavailable. In contrast to our previously reported β-carbon elimination, cyclization of a variety of 2-alkenylaniline substrates under electrophilic palladium conditions unexpectedly afforded C3-substituted indoles. This unusual 1,2-migratory process was found to be operative across a variety of substrates with predictable migratory aptitude. A mechanistic proposal was put forward to rationalize the observed substrate dependence, and this unexpected finding could provide an opportunity for other related processes.

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Citations

Jul 15, 2016·The Journal of Organic Chemistry·Salaheddin A I SharifAndrew Sutherland
Mar 21, 2020·Organic & Biomolecular Chemistry·Chuangchuang XuJiaxi Xu
Jun 16, 2018·Journal of Molecular Modeling·Xinghui ZhangYun Lei
Jul 28, 2021·The Journal of Organic Chemistry·Yun-Tao ZhengHai-Chao Xu
Oct 23, 2018·The Journal of Organic Chemistry·Anton S MakarovVladimir Gevorgyan
May 26, 2017·Journal of the American Chemical Society·Takuma WatanabeShinichi Saito
Jan 14, 2020·Organic Letters·Anand H Shinde, Shyam Sathyamoorthi

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