Tuning Regioselectivity of Wacker Oxidation in One Catalytic System: Small Change Makes Big Step

A regioselectivity switchable aerobic Wacker–Tsuji oxidation has been developed using catalytic tert-butyl nitrite as a simple organic redox cocatalyst. By solely switching the solvent, either substituted aldehydes or ketones could be prepared under mild aerobic conditions in good yields, respective...

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Published inJournal of organic chemistry Vol. 83; no. 18; pp. 11327 - 11332
Main Authors Hu, Kang-Fei, Ning, Xiao-Shan, Qu, Jian-Ping, Kang, Yan-Biao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.09.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM
ALKENES
KETONES
CROSS-COUPLING REACTION
PROTECTED ALLYLIC AMINES
OLEFINS
ALDEHYDES
TERMINAL OXIDANT
EFFICIENT
MOLECULAR-OXYGEN
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Summary:A regioselectivity switchable aerobic Wacker–Tsuji oxidation has been developed using catalytic tert-butyl nitrite as a simple organic redox cocatalyst. By solely switching the solvent, either substituted aldehydes or ketones could be prepared under mild aerobic conditions in good yields, respectively. A mechanistic explanation for the selectivity control is proposed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01547