Journal
ACS CATALYSIS
Volume 9, Issue 5, Pages 4196-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b00688
Keywords
remote; 1,n-arylamination; alkene isomerization; palladium; regioselectivity
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Funding
- National Natural Science Foundation of China [NSFC21572272]
- Foundation of the Open Project of State Key Laboratory of Natural Medicines [SKLNMZZCX201818]
- Innovation Team of the Double-First Class Disciplines [CPU2018GY04, CPU2018GY35]
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A palladium-catalyzed remote 1,n-arylamination (from 1,3- to 1,11-arylamination) of unactivated terminal alkenes with aryl iodides and arylamines has been realized. This three-component reaction proceeded via Pd-catalyzed Heck arylation, alkene isomerization, and aza-Michael addition, exhibiting good regio- and chemoselectivity, and wide substrate scope. Preliminary mechanistic studies indicated that the in situ generated ortho/para-quinone methide intermediates served as the driving force for the alkene isomerization and promoted the rearomatization upon nucleophilic amination.
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