Rh(III)-Catalyzed meta-C–H Alkenylation with Alkynes

Rh­(III)-catalyzed meta-C–H functionalization reactions are still rare. Herein, we report the first example of Rh­(III)-catalyzed meta-C–H alkenylation with disubstituted alkynes directed by a U-shaped nitrile template. Exclusive regio-selectivity has been achieved using unsymmetrical aryl and alkyl...

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Published inJournal of the American Chemical Society Vol. 141; no. 1; pp. 76 - 79
Main Authors Xu, Hua-Jin, Kang, Yan-Shang, Shi, Hang, Zhang, Ping, Chen, You-Ke, Zhang, Bing, Liu, Zhi-Qiang, Zhao, Jing, Sun, Wei-Yin, Yu, Jin-Quan, Lu, Yi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.01.2019
Amer Chemical Soc
Subjects
alkynes
catalysts
Chemistry
Chemistry, Multidisciplinary
palladium
Physical Sciences
Science & Technology
DIRECTING GROUP
CATALYSIS
ACTIVATION
OLEFINATION
ALKYLATION
ARYLATION
ARENES
BOND FUNCTIONALIZATION
LIGAND
BORYLATION
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Summary:Rh­(III)-catalyzed meta-C–H functionalization reactions are still rare. Herein, we report the first example of Rh­(III)-catalyzed meta-C–H alkenylation with disubstituted alkynes directed by a U-shaped nitrile template. Exclusive regio-selectivity has been achieved using unsymmetrical aryl and alkyl-disubstituted alkynes to afford synthetically valuable trisubstituted olefins. Propargyl alcohols are also compatible, affording complex allylic alcohols. Notably, transition metal-catalyzed meta-alkenylation with alkynes has not been successful with Pd catalysts.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.8b11038