Synthesis of Branch-Type 3-Allylindoles from N-Alkyl- N-cinnamyl-2-ethynylaniline Derivatives Using π-Allylpalladium Chloride Complex as a Catalyst

Kohei Watanabe; Keita Nakano; Hayato Sato; Toshiki Yamaoka; Yasushi Yoshida; Ryo Takita; Yoshio Kasashima; Masami Sakamoto; Takashi Mino

doi:10.1021/acs.joc.4c00771

Synthesis of Branch-Type 3-Allylindoles from N-Alkyl- N-cinnamyl-2-ethynylaniline Derivatives Using π-Allylpalladium Chloride Complex as a Catalyst

J Org Chem. 2024 May 10. doi: 10.1021/acs.joc.4c00771. Online ahead of print.

Authors

Kohei Watanabe¹, Keita Nakano², Hayato Sato², Toshiki Yamaoka², Yasushi Yoshida^{2

3

4}, Ryo Takita⁵, Yoshio Kasashima⁶, Masami Sakamoto², Takashi Mino^{2

3

4}

Affiliations

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
² Graduate School of Engineering, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
³ Molecular Chirality Research Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
⁴ Soft Molecular Activation Research Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
⁵ School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
⁶ Education Center, Chiba Institute of Technology, Shibazono 2-2-1, Narashino, Chiba 275-0023, Japan.

PMID: 38728550
DOI: 10.1021/acs.joc.4c00771

Abstract

The reaction of N-alkyl-N-cinnamyl-2-ethynylaniline derivatives 1 via annulation and aza-Claisen-type rearrangement easily afforded corresponding branch-type 3-allylindoles 2 with high regioselectivities in good yields using π-allylpalladium chloride complex as a catalyst.