Organophosphine-Catalyzed Intramolecular Hydroacylation of Activated Alkynes

We present the details of an organophosphine-catalyzed Morita–Baylis–Hillman-type reaction of activated alkynes. The outcome is an intramolecular hydroacylation of α,β-ynones leading to the formation of 1,3-cyclopenta-, cyclohepta-, and cyclooctadione-fused arenes and heteroarenes. In addition, duri...

Full description

Saved in:
Bibliographic Details
Published in:ACS catalysis 2018-04, Vol.8 (4), p.2748-2753
Main Authors: Mondal, Atanu, Hazra, Raju, Grover, Jagdeep, Raghu, Moluguri, Ramasastry, S. S. V
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We present the details of an organophosphine-catalyzed Morita–Baylis–Hillman-type reaction of activated alkynes. The outcome is an intramolecular hydroacylation of α,β-ynones leading to the formation of 1,3-cyclopenta-, cyclohepta-, and cyclooctadione-fused arenes and heteroarenes. In addition, during the course of the investigation, a phosphine-catalyzed intramolecular aldol reaction of keto-ynones via δ′[C­(sp3)-H]-functionalization was discovered, and a new annulation event comprising of a ω′[C­(sp3)-H]-functionalization of α,β-ynones was also uncovered. The mechanisms governing these processes have been thoroughly elucidated.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b00397