Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 1, Pages 312-316Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201811522
Keywords
aldehydes; carboxylic acids; deoxygenation; deuteration; synergistic catalysis
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Funding
- National Natural Science Foundation of China [21702098, 21672099, 21732003, 21703118]
- Fundamental Research Funds for the Central Universities [020514380158, 020514380131]
- Shandong Provincial Natural Science Foundation [ZR2017MB038]
- 1000-Youth Talents Plan
- Nanjing University
- Nanjing University [CXCY17-19]
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We report a general, practical, and scalable means of preparing deuterated aldehydes from aromatic and aliphatic carboxylic acids with D2O as an inexpensive deuterium source. The use of Ph3P as an O-atom transfer reagent can facilitate the deoxygenation of aromatic acids, while Ph2POEt 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.
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