化学
小学(天文学)
基质(水族馆)
烯烃
酰胺
酮
氢化物
炔烃
磷化氢
产量(工程)
立体选择性
组合化学
催化作用
有机化学
氢
材料科学
冶金
地质学
物理
海洋学
天文
作者
R. Justin Grams,Monsurat M. Lawal,Connor Szwetkowski,Daniel J. Foster,Carol Ann Rosenblum,Carla Slebodnick,Valerie Vaissier Welborn,Webster L. Santos
标识
DOI:10.1002/adsc.202101020
摘要
Abstract We report a chemoselective, phosphine‐catalyzed semireduction of primary and secondary propiolamides. In the presence of stoichiometric pinacolborane and catalytic n ‐tributylphosphine, a variety of propiolamides were successfully converted to the corresponding acrylamides in excellent yield with ( E )‐stereoselectivity. The reaction condition is tolerant of various functional groups including alkene, alkyne, ketone, or ester. Deuterium labeling studies established that the hydride from activated pinacolborane is added to the α‐carbon and the proton on the amide nitrogen is abstracted by the ß‐carbon to furnish the ( E )‐acrylamides. DFT calculations revealed a clear energetic driving force for the ( E )‐ over the ( Z )‐isomer. magnified image
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