Rhodium-Catalyzed Successive C–H Bond Functionalizations To Synthesize Complex Indenols Bearing a Benzofuran Unit

An efficient rhodium-catalyzed redox-neutral annulations of N-phenoxyacetamides and ynones via successive double C–H bond activations has been developed. A series of novel and complex indenols bearing a benzofuran unit were generated with moderate to excellent regioselecetivities under mild conditio...

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Published inOrganic letters Vol. 21; no. 23; pp. 9598 - 9602
Main Authors Mei, Yan-Le, Zhou, Wei, Huo, Tao, Zhou, Fang-Shuai, Xue, Jing, Zhang, Guang-Yi, Ren, Bing-Tao, Zhong, Cheng, Deng, Qing-Hai
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.12.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIRECTING GROUPS
KETONES
ACTIVATION
PRIVILEGED SCAFFOLD
ANNULATION
DRUG DISCOVERY
CARBOCYCLIZATION
ALKYNES
DERIVATIVES
N-PHENOXYACETAMIDES
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Summary:An efficient rhodium-catalyzed redox-neutral annulations of N-phenoxyacetamides and ynones via successive double C–H bond activations has been developed. A series of novel and complex indenols bearing a benzofuran unit were generated with moderate to excellent regioselecetivities under mild conditions. Adding N-ethylcyclo­hexanamine (CyNHEt) could restrict the formation of the mono C–H bond activation byproduct, which is not the intermediate of the reaction demonstrated via the mechanistic investigations.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03766