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Deoxygenative Deuteration of Carboxylic Acids with D 2 O
Author(s) -
Zhang Muliang,
Yuan XiangAi,
Zhu Chengjian,
Xie Jin
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201811522
Subject(s) - deoxygenation , chemistry , reagent , organic chemistry , deuterium , natural product , carboxylic acid , combinatorial chemistry , medicinal chemistry , catalysis , physics , quantum mechanics
We report a general, practical, and scalable means of preparing deuterated aldehydes from aromatic and aliphatic carboxylic acids with D 2 O as an inexpensive deuterium source. The use of Ph 3 P as an O‐atom transfer reagent can facilitate the deoxygenation of aromatic acids, while Ph 2 POEt is a better O‐atom transfer reagent for aliphatic acids. The highly precise deoxygenation of complex carboxylic acids makes this protocol promising for late‐stage deoxygenative deuteration of natural product derivatives and pharmaceutical compounds.