Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 11, Pages 7370-7380Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00259
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Funding
- National Natural Science Foundation of China [21772001]
- Anhui Provincial Natural Science Foundation [1808085MB41]
- Cultivation Project for University Outstanding Talents of Anhui Province
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The Rh(III)-catalyzed cascade nucleophilic addition/intramolecular annulation of 2-diazo-1,3-diketones with 1,3-dicarbonyl compounds has been successfully achieved to yield 6,7-dihydrobenzofuran-4(5H)-ones in up to 91% yields. The reaction tolerates a wide range of substrates and functional groups under optimized conditions and is scalable and adaptable to late-stage functionalization.
A Rh(III)-catalyzed cascade nucleophilic addition/intramolecular annulation of 2-diazo-1,3-diketones with 1,3-dicarbonyl compounds (e.g., 1,3-diketones and beta-keto esters) is achieved to afford 6,7-dihydrobenzofuran-4(5H)-ones in up to 91% yields. Notably, a wide range of substrates and functional groups were well-tolerated under the optimized reaction conditions to give desired products in moderate to excellent yields with release of N-2 and H2O as byproducts. Moreover, the method described is scalable and adaptable to late-stage functionalization.
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