Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 18, Pages 11623-11638Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01557
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Funding
- National Natural Science Foundation of China [21772001]
- Anhui Provincial Natural Science Foundation [1808085MB41]
- Special and Excellent Research Fund of Anhui Normal University
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A simple, general route to the 2,3-dihydrobenzofurans substituted at C3 by an aryethynyl or aryl group, starting from propargylamine and its derivatives with benzoyl sulfonium salts, has been developed. This reaction involved an in situ generated o-quinone methide (o-QM) intermediate followed by [4+1] annulation with sulfur ylides. Notably, this protocol's features include moderate to excellent yields and remarkable diastereoselectivity (>20:1 dr in general), easy performance, as well as applicability to versatile 2,3-dihydrobenzofurans with aryethynyl or an aryl group via C-C and C-O bond formation in one pot without any catalyst in an aqueous mixed solvent.
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