Research ArticleORGANIC CHEMISTRY

Rhodium-catalyzed, P-directed selective C7 arylation of indoles

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Science Advances  14 Dec 2018:
Vol. 4, no. 12, eaau6468
DOI: 10.1126/sciadv.aau6468

Abstract

The indole scaffold will continue to play a vital role in the future of drug discovery and agrochemical development. Regioselective direct arylation of indoles on the benzenoid moiety is a challenging task due to the inherent reactivity of the C2 and C3 positions. Here, we have developed an effective strategy for the regioselective direct arylation of indoles at the C7 position with (hetero)aryl bromides by the rational design of a directing group. The key to the high selectivity and reactivity of this method is the appropriate selection of a class of directing groups, N-PR2 (R = tBu and cHex), that are easily removed in the presence of the Wilkinson’s catalyst. Using the present method as a key step, formal synthesis of marine alkaloid dictyodendrin B has also been demonstrated.

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