2024-03-29T07:59:22Z
https://nagoya.repo.nii.ac.jp/oai
oai:nagoya.repo.nii.ac.jp:02002053
2023-01-16T04:59:03Z
1903:1904:1905
Cobalt/Organophotoredox Dual-Catalysis-Enabled Cascade Cyclization of 1,6-Diynyl Esters via Formal 1,8-Acyloxy Migration
Yasui, Takeshi
Yamada, Keiji
Tatsumi, Rine
Yamamoto, Yoshihiko
open access
This document is the Accepted Manuscript version of a Published Work that appeared in final form in [ACS Catalysis], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [https://pubs.acs.org/articlesonrequest/AOR-GSDTA64GIRD3EB27CCTY].”
cobalt catalysis
metallaphotoredox
cycloaddition
allenes
cascade reaction
Herein, we report a method for the generation of vinylallenes via cobalt/photoredox dual-catalysis-enabled formal 1,8-acyloxy migration of 1,6-diynyl esters. We demonstrated a 1,8-acyloxy migration/6π-electrocyclization cascade using (hetero)aryl-substituted 1,6-diynyl esters as substrates, leading to the formation of arenol derivatives. Several control experiments suggested that the β-oxygen elimination of a cobaltacyclopentadiene intermediate enabled formal 1,8-acyloxy migration to generate the vinylallene. We also applied this method to cascade cyclizations involving [2 + 2] or [4 + 2] cycloadditions to furnish various polycyclic molecules.
ACS Publications
2022-09-17
2021-09-17
eng
journal article
AM
http://hdl.handle.net/2237/0002002053
https://nagoya.repo.nii.ac.jp/records/2002053
https://doi.org/10.1021/acscatal.1c03704
2155-5435
ACS Catalysis
11
18
11716
11722
https://nagoya.repo.nii.ac.jp/record/2002053/files/ACS_Catal-2.pdf
application/pdf
621 KB
2022-09-17