Catalytic Multisite-Selective Acetoxylation Reactions at sp(2) vs sp(3) C-H Bonds in Cyclic Olefins

The first Pd-catalyzed multisite-selective acetoxylation reactions are disclosed at an unactivated alkene sp(2) C-H bond versus secondary allylic sp(3) C-H bond in cyclic olefins via the modulation of directing groups. The different directing groups overcome the-key challenge in differentiating C-H...

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Published inOrganic letters Vol. 18; no. 19; pp. 5014 - 5017
Main Authors Zang, Zhong-Lin, Zhao, Sheng, Karnakanti, Shuklachary, Liu, Cheng-Lin, Shao, Pan-Lin, He, Yun
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 07.10.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIRECTING GROUP
FUNCTIONALIZATION
ORGANIC-SYNTHESIS
C(SP)-H BONDS
PALLADIUM
ACTIVATION
ALLYLIC OXIDATION
COPPER
C(SP)-H
TERMINAL ALKENES
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Summary:The first Pd-catalyzed multisite-selective acetoxylation reactions are disclosed at an unactivated alkene sp(2) C-H bond versus secondary allylic sp(3) C-H bond in cyclic olefins via the modulation of directing groups. The different directing groups overcome the-key challenge in differentiating C-H bonds and provide a new controlling approach for site-specific C-H activation. A wide variety of substrates are readily acetoxylated under operationally simple conditions. Mechanistic studies suggest that different Pd (IV) intermediates were involved in the multisite-selective acetoxylation reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02458