Department of Chemistry, Indian Institute of Technology Madras , Chennai - 600036, India.
J Org Chem. 2017 Dec 1;82(23):12328-12336. doi: 10.1021/acs.joc.7b02161. Epub 2017 Nov 20.
Efficient and general one-pot trifluoromethylative functionalization of amides has been accomplished for the synthesis of various trifluoromethylated bis(indolyl)arylmethane, utilizing trifluoromethyltrimethylsilane and substituted indoles as nucleophiles. The developed reaction involves the in situ generation and trapping of a trifluoromethylated iminium ion, derived from the trifluoromethylated hemiaminal of amide, with various substituted indoles. This method has been successfully extended to the synthesis of diverse trifluoromethylated triarylmethanes employing phenols as nucleophiles. Furthermore, the potential of the method was demonstrated via the two-step synthesis of a trifluoromethylated analog of a hypolipidemic and anti-obesity agent.
酰胺的高效、通用一锅法三氟甲基化官能化反应已经完成，用于合成各种三氟甲基化双（吲哚基）芳基甲烷，利用三氟甲基三甲基硅烷和取代吲哚作为亲核试剂。所开发的反应涉及酰胺的三氟甲基半亚胺的原位生成和捕获，与各种取代吲哚反应形成三氟甲基化亚胺离子。该方法已成功扩展到使用酚作为亲核试剂合成各种三氟甲基化三芳基甲烷。此外，通过两步法合成降脂和抗肥胖药物的三氟甲基类似物证明了该方法的潜力。
