Transition-metal-free cross-coupling of indium organometallics with chromene and isochroman acetals mediated by BF3•OEt2.

Gil-Negrete, J. M.; Pérez Sestelo, J.; Sarandeses, L. A.


Org. Lett. 2016, 18, 4316–4319 (DOI: 10.1021/acs.orglett.6b02058).

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Highlighted in: Knochel, P.; Hammann, J. M. Synfacts 2016, 12, 1185 (DOI: 10.1055/s-0036-1589323).

A transition-metal-free coupling of triorganoindium reagents with benzopyranyl acetals mediated by a Lewis acid has been developed. The reaction of R3In with chromene and isochroman acetals in the presence of BF3·OEt2 afforded 2-substituted chromenes and 1-substituted isochromans, respectively, in good yields. The reactions proceed with a variety of triorganoindium reagents (aryl, heteroaryl, alkynyl, alkenyl, alkyl) using only 50 mol% of the organometallic, thus demonstrating the efficiency of these species. Preliminary mechanistic studies indicate the formation of an oxocarbenium ion intermediate in the presence of the Lewis acid.