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Pentafluorophenyl Esters: Highly Chemoselective Ketyl Precursors for the Synthesis of α,α-Dideuterio Alcohols Using SmI2 and D2O as a Deuterium Source.
Organic Letters ( IF 5.2 ) Pub Date : 2020-01-08 , DOI: 10.1021/acs.orglett.9b04383
Hengzhao Li 1 , Yuxia Hou 1 , Chengwei Liu 2 , Zemin Lai 1 , Lei Ning 1 , Roman Szostak 3 , Michal Szostak 2 , Jie An 1
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We report the first highly chemoselective synthesis of α,α-dideuterio alcohols with exquisite incorporation of deuterium (>98% [D2]) using pentafluorophenyl esters as ketyl radical precursors, SmI2 as a mild reducing agent, and D2O as the deuterium source. This system tolerates a variety of functional groups, offering rapid entry to valuable α,α-dideuterated alcohol building blocks. More generally, this report introduces pentafluorophenyl esters as the most reactive O-ketyl precursors reported to date.

中文翻译:

五氟苯基酯:使用SmI2和D2O作为氘源,用于化学合成α,α-二氘代乙醇的高度化学选择性的乙炔基前体。

我们报道了使用五氟苯基酯作为酮基自由基前体,SmI2作为温和的还原剂以及D2O作为氘源的氘(≥98%[D2])的精细掺入,首次高度化学选择性地合成α,α-二氘代乙醇。该系统可耐受多种功能基团,可快速进入有价值的α,α-二氘代醇构建基块。更一般地,该报告介绍了五氟苯基酯,这是迄今为止报道的最具反应性的O-酮基前体。
更新日期:2020-01-08
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