- C?H Alkenylation of Pyrroles by Electronically Matching Ligand Control
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Directing group and substrate control strategies have frequently been employed for the regioselective C?H alkenylation of acid- and oxidant-sensitive pyrrole heterocycles. We developed an undirected, aerobic strategy for the C?H alkenylation of N-alkylpyrroles by ligand control. For C2-alkenylation of electron-rich N-alkylpyrroles, an electrophilic palladium catalyst derived from Pd(OAc)2 and 4,5-diazafluoren-9-one (DAF) was used. Alternatively, a combination of Pd(OAc)2 and a mono-protected amino acid ligand, Ac-Val-OH, was useful for C5-alkenylation of N-alkylpyrroles possessing electron-withdrawing groups at the C2 position. This approach based on the electronic effects of heterocycles and catalysts can rapidly provide a wide range of alkenyl pyrroles from readily available N-alkylpyrroles and alkenes.
- Kim, Hyun Tae,Lee, Woohyeong,Kim, Eunmin,Joo, Jung Min
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supporting information
p. 2418 - 2422
(2018/09/10)
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- N-(lower alkyl)-2-(3'ureidobenzyl)pyrrolidines
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N-(lower alkyl)-2-(3'-ureidobenzyl)pyrrolidines and N-(lower alkyl)-2-(3'-ureidobenzyl)-5-(lower alkyl)pyrrolidines are useful for lowering intraocular pressure in mammals, for example, in the treatment of glaucoma.
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