Br2-Catalyzed regioselective dehydrative coupling of indoles with acyloins: direct synthesis of α-(3-indolyl) ketones
作者： Deqiang Liang , Xiangguang Li , Yanni Li , Yungang Yang , Shulin Gao
DOI: 10.1039/C6RA03321K
关键词: Organic chemistry 、 Catalysis 、 Density functional theory 、 Regioselectivity 、 Selectivity 、 Hydrogen bond 、 Carbocation 、 Combinatorial chemistry 、 Chemistry 、 Hydrogen 、 Substrate (chemistry)
摘要: An efficient Br2-catalyzed synthesis of α-(3-indolyl) ketones via dehydrative coupling simple indoles with acyloins is presented. This reaction proceeded high C-3 selectivity and a wide substrate scope, without any metal catalyst. Both the activation alcohols by carbonyl groups catalysis Br2 were essential. Density functional theory (DFT) calculations indicated that not only enhanced electrophilicities resulting carbocations, but acted as stabilizers for them well, catalyst hydrogen bonding between hydroxyl was key process this transformation.
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