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

Kishore, Dakoju Ravi and Satyanarayana, G. (2022) Intermolecular Sonogashira Coupling and Intramolecular 5-Exo-dig Cycloisomerization Cascade: A One-Pot Pathway for Accessing (3-Benzylbenzofuran-2-yl)(phenyl)methanones. The Journal of Organic Chemistry. pp. 1-15. ISSN 0022-3263

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Abstract

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.

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IITH Creators:

IITH Creators	ORCiD
Satyanarayana, G.	UNSPECIFIED

Item Type:

Article

Additional Information:

The authors gratefully acknowledge the financial support from DST-SERB (Department of Science and Technology, Science and Engineering Research Board, Grant EMR/2017/005312) , New Delhi. D.R.K gratefully acknowledges UGC for providing the fellowship.

Uncontrolled Keywords:

CATALYZED DOMINO REACTIONS,BENZOFURANS,CYCLIZATION ,ANNULATION PHENOLS ,ETHER

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

01 Aug 2022 09:35

Last Modified:

01 Aug 2022 09:35