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 in | Chemical communications (Cambridge, England) Vol. 60; no. 100; pp. 15031 - 15034 |
|---|---|
| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
12.12.2024
Royal Society of Chemistry |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1359-7345 1364-548X 1364-548X |
| DOI | 10.1039/D4CC06072E |
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| Abstract | 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. |
|---|---|
| AbstractList | 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. 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.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. 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. 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 a Catellani reaction that involves sequential -C-H alkylation and -C-N bond cleavage annulation of primary benzamides. Employing norbornadiene (NBD) instead of NBE enables the assembly of -alkylamines by an intermolecular hydroamination reaction. |
| Author | Chen, Ming Li, Wentao Cao, Man Li, Wenguang Sheng, Heyun Zhang, Xu Li, Ting Gao, Wenchao Cheng, Xinfeng Yu, Yongqi |
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| Snippet | A palladium-catalyzed divergent reaction of primary benzamides using norbornene (NBE) derivatives as a controlled switch is reported. When NBE is used as a... |
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| SubjectTerms | Alkylamines Alkylation Chemical reactions Chemical synthesis Chemistry Chemistry, Multidisciplinary Organic chemistry Palladium Physical Sciences Science & Technology |
| Title | Palladium-catalyzed annulation and intermolecular hydroamination involving norbornene derivatives: synthesis of indanones and N -alkylamines |
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