Intermolecular Sonogashira Coupling and Intramolecular 5-Exo-dig Cycloisomerization Cascade: A One-Pot Pathway for Accessing (3-Benzylbenzofuran-2-yl)(phenyl)methanones
Dakoju Ravi Kishore and Gedu Satyanarayana*
*Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy District, 502284 Hyderabad, Telangana, India,
Email: gvsatya
chy.iith.ac.in
D. R. Kishore, G. Satyanarayana, J. Org. Chem., 2022, 87, 10158-10172.
DOI: 10.1021/acs.joc.2c01101
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Abstract
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 provide 2,3-disubstituted benzo[b]furans.
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proposed mechanism
Key Words
benzofurans, Sonogashira coupling, acetylenes, cyclization, palladium catalysis
ID: J42-Y2022
