Intermolecular Sonogashira Coupling and Intramolecular 5-Exo-dig Cycloisomerization Cascade: A One-Pot Pathway for Accessing (3-Benzylbenzofuran-2-yl)(phenyl)methanones

Herein, we present an efficient and straightforward strategy enabling access to 2,3-disubstituted benzo­[b]­furans. The whole synthetic process proceeds via a domino intermolecular Sonogashira coupling of 2-(2-bromophenoxy)-1-phenylethan-1-ones/alkyl 2-(2-bromophenoxy)­acetates/2-(2-bromophenoxy)­ac...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2022-08, Vol.87 (15), p.10158-10172
Main Authors: Kishore, Dakoju Ravi, Satyanarayana, Gedu
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:Herein, we present an efficient and straightforward strategy enabling access to 2,3-disubstituted benzo­[b]­furans. The whole synthetic process proceeds via a domino intermolecular Sonogashira coupling of 2-(2-bromophenoxy)-1-phenylethan-1-ones/alkyl 2-(2-bromophenoxy)­acetates/2-(2-bromophenoxy)­acetonitrile/1-(2-bromophenoxy)­propan-2-one with terminal acetylenes followed by an intramolecular carbanion-yne cyclization in a 5-exo-dig manner and subsequent double-bond isomerization. Notably, two C–C bonds have been constructed in a one-pot manner and a wide variety of (3-benzylbenzofuran-2-yl)­(phenyl)­methanones were accomplished with good functional group tolerance.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01101