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Synthesis of 2,3-Dihydrobenzofurans

Recent Literature


A bifunctional aminoboronic acid facilitates intramolecular aza- and oxa-Michael reactions of α,β-unsaturated carboxylic acids. The combination of an arylboronic acid with a chiral aminothiourea enables enantioselective conversions to afford the desired heterocycles in high yields and ee’s (up to 96% ee).
T. Azuma, A. Murata, Y. Kobayashi, T. Inokuma, Y. Takemoto, Org. Lett., 2014, 16, 4256-4259.


A phosphorus(III)-mediated formal [4+1]-cycloaddition of 1,2-dicarbonyls and o-quinone methides provides 2,3-dihydrobenzofurans. Subtle steric interactions involved in the [4+1]-cycloannulation have an impact on yield and stereoselectivity in dihydrobenzofuran formation.
K. X. Rodriguez, J. D. Vail, B. L. Ashfeld, J. Zhu, Org. Lett., 2016, 18, 4514-4517.


Fluoride-induced desilylation of 2-bromo-1-{2-[(triisopropylsilyl)oxy]phenyl}ethyl nitrate enables a regioselective one-pot synthesis of 3-substituted 2,3-dihydrobenzofurans via generation of o-quinone methides followed by Michael addition of different C, N, O, and S nucleophiles, and intramolecular 5-exo-tet elimination of a bromide anion. The method has potential synthetic applications in drug discovery.
A. k. Shaikh, G. Varvounis, Org. Lett., 2014, 16, 1478-1481.