Photocatalytic Regioselective Difunctionalization of Alkenes with Diazo Compounds and tert-Butyl Nitrite: Access to ?-Oximino Esters

A visible-light photocatalytic regioselective difunc-tionalization of alkenes with diazo compounds and tert-butyl nitrite has been developed. The protocol provides an efficient approach to gamma-oximino esters under mild conditions. Significantly, this trans -formation not only shows the good compat...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 37; pp. 6834 - 6838
Main Authors Liu, Yantao, Zhu, Keyong, Zhao, Jingjing, Li, Pan
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 08.09.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MILD
CARBENE
CATALYSIS
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Summary:A visible-light photocatalytic regioselective difunc-tionalization of alkenes with diazo compounds and tert-butyl nitrite has been developed. The protocol provides an efficient approach to gamma-oximino esters under mild conditions. Significantly, this trans -formation not only shows the good compatibility of nucleophilic diazo compounds and electrophilic tert-butyl nitrite but also displays diazo compounds generating alkyl radicals that preferred addition to alkenes over nitroso radicals.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02749