NDLI: Palladium(II)-catalyzed allylic C-H oxidation of hindered substrates featuring tunable selectivity over extent of oxidation.

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Palladium(II)-catalyzed allylic C-H oxidation of hindered substrates featuring tunable selectivity over extent of oxidation.

Content Provider	Semantic Scholar
Author	Xing, Xiangyou O'Connor, Nicholas R. Stoltz, Brian M.
Copyright Year	2015
Abstract	The use of Oxone and a palladium(II) catalyst enables the efficient allylic CH oxidation of sterically hindered α-quaternary lactams which are unreactive under known conditions for similar transformations. This simple, safe, and effective system for CH activation allows for unusual tunable selectivity between a two-electron oxidation to the allylic acetates and a four-electron oxidation to the corresponding enals, with the dominant product depending on the presence or absence of water. The versatile synthetic utility of both the allylic acetate and enal products accessible through this methodology is also demonstrated.
Starting Page	124
Ending Page	142
Page Count	19
File Format	PDF HTM / HTML
Alternate Webpage(s)	http://authors.library.caltech.edu/59302/2/anie_201504007_sm_miscellaneous_information.pdf
PubMed reference number	26234251v1
Alternate Webpage(s)	https://doi.org/10.1002/anie.201504007
DOI	10.1002/anie.201504007
Journal	Angewandte Chemie
Volume Number	54
Issue Number	38
Language	English
Access Restriction	Open
Subject Keyword	Germine Acetates Lactams Palladium allylic sulfur ylide cell transformation medroxyprogesterone acetate oxidation potassium peroxymonosulfuric acid
Content Type	Text
Resource Type	Article

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