Halogen Bond-Catalyzed Friedel–Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes

The use of a halogen bond donor to catalyze Friedel–Crafts reactions of indoles with a range of aldehydes and ketones to directly produce bis­(indolyl)­methanes, including the natural products arsindoline A, arundine, trisindoline, and vibrindole A, is reported. The bidentate catalyst used in these...

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Veröffentlicht in:Organic letters 2019-11, Vol.21 (22), p.9212-9216
Hauptverfasser: Liu, Xuelei, Ma, Shuang, Toy, Patrick H
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container_title Organic letters
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creator Liu, Xuelei
Ma, Shuang
Toy, Patrick H
description The use of a halogen bond donor to catalyze Friedel–Crafts reactions of indoles with a range of aldehydes and ketones to directly produce bis­(indolyl)­methanes, including the natural products arsindoline A, arundine, trisindoline, and vibrindole A, is reported. The bidentate catalyst used in these reactions proved to be more effective than a monondentate analogue, a thiourea commonly used as an organocatalyst, and even a trityl cation that has been used previously in the synthesis of bis­(indolyl)­methanes.
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title Halogen Bond-Catalyzed Friedel–Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes
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