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  • Palladium/Norbornene‐Catalyzed Direct Vicinal Di‐Carbo‐Functionalization of Indoles: Reaction Development and Mechanistic Study
Title: Palladium/Norbornene‐Catalyzed Direct Vicinal Di‐Carbo‐Functionalization of Indoles: Reaction Development and Mechanistic Study
Abstract Methods that can simultaneously install multiple different functional groups to heteroarenes via C−H functionalizations are valuable for complex molecule synthesis, which, however, remain challenging to realize. Here we report the development of vicinal di‐carbo‐functionalization of indoles in a site‐ and regioselective manner, enabled by the palladium/norbornene (Pd/NBE) cooperative catalysis. The reaction is initiated by the Pd(II)‐mediated C3‐metalation and specifically promoted by the C1‐substituted NBEs. The mild, scalable, and robust reaction conditions allow for a good substrate scope and excellent functional group tolerance. The resulting C2‐arylated C3‐alkenylated indoles can be converted to diverse synthetically useful scaffolds. The combined experimental and computational mechanistic study reveals the unique role of the C1‐substituted NBE in accelerating the turnover‐limiting oxidative addition step.  more » « less
Award ID(s):
2247505
PAR ID:
10469428
Author(s) / Creator(s):
 ;  ;  ;  ;  ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
Angewandte Chemie International Edition
Volume:
62
Issue:
43
ISSN:
1433-7851
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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