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 β-keto esters) is achieved to afford 6,7-dihydrobenzofuran-4(5)-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 and HO as byproducts. Moreover, the method described is scalable and adaptable to late-stage functionalization.
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http://dx.doi.org/10.1021/acs.joc.1c00259 | DOI Listing |
Chem Commun (Camb)
January 2019
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, China.
Three-component C-H bond additions across two different coupling partners remain underdeveloped. Herein, we report the first three-component RhIII-catalyzed C-H bond additions to a wide range of dienes and aldehydes. Our method constitutes a complementary access with Ellman's CoIII-catalytic system to homoallylic alcohols.
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