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

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 effectiv...

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Published inScience advances Vol. 4; no. 12; p. eaau6468
Main Authors Qiu, Xiaodong, Deng, Hong, Zhao, Yue, Shi, Zhuangzhi
Format Journal Article
LanguageEnglish
Published United States American Association for the Advancement of Science 01.12.2018
Subjects
Chemistry
Organic Chemistry
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Summary: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-PR (R = Bu and Hex), 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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ISSN:2375-2548
2375-2548
DOI:10.1126/sciadv.aau6468