Palladium-catalyzed annulation and intermolecular hydroamination involving norbornene derivatives: synthesis of indanones and N -alkylamines

A palladium-catalyzed divergent reaction of primary benzamides using norbornene (NBE) derivatives as a controlled switch is reported. When NBE is used as a mediator, indanones are synthesized with moderate to good yields via a Catellani reaction that involves sequential ortho -C–H alkylation and ips...

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Published inChemical communications (Cambridge, England) Vol. 60; no. 100; pp. 15031 - 15034
Main Authors Li, Wenguang, Cheng, Xinfeng, Cao, Man, Sheng, Heyun, Gao, Wenchao, Chen, Ming, Zhang, Xu, Li, Wentao, Yu, Yongqi, Li, Ting
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 12.12.2024
Royal Society of Chemistry
Subjects
Alkylamines
Alkylation
Chemical reactions
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Organic chemistry
Palladium
Physical Sciences
Science & Technology
FUNCTIONALIZATION
ALKENES
KETONES
CARBOPALLADATION
ALKYNES
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ISSN1359-7345
1364-548X
1364-548X
DOI10.1039/D4CC06072E

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Summary:A palladium-catalyzed divergent reaction of primary benzamides using norbornene (NBE) derivatives as a controlled switch is reported. When NBE is used as a mediator, indanones are synthesized with moderate to good yields via a Catellani reaction that involves sequential ortho -C–H alkylation and ipso -C–N bond cleavage annulation of primary benzamides. Employing norbornadiene (NBD) instead of NBE enables the assembly of N -alkylamines by an intermolecular hydroamination reaction.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/D4CC06072E