Development of Cycloisomerization with Rearrangement of a Tosyl Group Using N-Tosyl- o-allenylaniline

Shohei Yoshioka; Masaharu Takatsuki; Tsunayoshi Takehara; Takeyuki Suzuki; Mitsuhiro Arisawa

doi:10.1021/acs.joc.3c00625

Development of Cycloisomerization with Rearrangement of a Tosyl Group Using N-Tosyl- o-allenylaniline

J Org Chem. 2023 Aug 4;88(15):11268-11277. doi: 10.1021/acs.joc.3c00625. Epub 2023 Jul 21.

Authors

Shohei Yoshioka¹, Masaharu Takatsuki¹, Tsunayoshi Takehara², Takeyuki Suzuki², Mitsuhiro Arisawa¹

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.
² Comprehensive Analysis Centre, SANKEN, Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan.

PMID: 37477559
DOI: 10.1021/acs.joc.3c00625

Abstract

Sulfonyl indoles were synthesized by migratory cycloisomerization from the allene N-tosyl-o-allenylaniline. 3-Tosyl indoles or 4-tosyl indoles were selectively produced using a Pd catalyst or a Au catalyst, respectively.