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Palladium-Catalyzed Synthesis of N-Vinyl Pyrroles and Indoles

Movassaghi, Mohammad and Ondrus, Alison E. (2005) Palladium-Catalyzed Synthesis of N-Vinyl Pyrroles and Indoles. Journal of Organic Chemistry, 70 (21). pp. 8638-8641. ISSN 0022-3263. PMCID PMC5548004. doi:10.1021/jo051450i. https://resolver.caltech.edu/CaltechAUTHORS:20170901-082320777

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Abstract

A stereospecific palladium-catalyzed N-vinylation of azaheterocycles with vinyl triflates is described. Cyclic and acyclic vinyl triflates along with nonnucleophilic azaheterocycles were found to be substrates for this palladium-catalyzed synthesis of N-vinyl pyrrole and indole derivatives.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo051450iDOIArticle
http://pubs.acs.org/doi/pdf/10.1021/jo051450iPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5548004/PubMed CentralArticle
http://pubs.acs.org/doi/suppl/10.1021/jo051450i/suppl_file/jo051450isi20050810_022543.pdfPublisherSupporting Information
Additional Information:© 2005 American Chemical Society. Received July 13, 2005. M.M. is a Dale F. and Betty Ann Frey Damon Runyon Scholar supported by the Damon Runyon Cancer Research Foundation (DRS-39-04). M.M. is a Firmenich Assistant Professor of Chemistry. A.E.O. acknowledges a Robert T. Haslam Presidential Graduate Fellowship. We thank Mr. Matthew P. Rainka and Professor Stephen L. Buchwald for helpful discussions. We thank Mr. Robert W. Sindelar for early contributions to this study. We acknowledge generous financial support by the donors of the American Chemical Society Petroleum Research Fund (40631G1), MIT, Amgen Inc., and NIH-NIGMS (GM074825).
Funders:
Funding AgencyGrant Number
Damon Runyon Cancer Research FoundationDRS-39-04
Robert T. Haslam Presidential Graduate FellowshipUNSPECIFIED
American Chemical Society Petroleum Research Fund40631G1
Massachusetts Institute of Technology (MIT)UNSPECIFIED
AmgenUNSPECIFIED
NIHGM074825
Issue or Number:21
PubMed Central ID:PMC5548004
DOI:10.1021/jo051450i
Record Number:CaltechAUTHORS:20170901-082320777
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170901-082320777
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:81057
Collection:CaltechAUTHORS
Deposited By: Donna Wrublewski
Deposited On:01 Sep 2017 17:38
Last Modified:15 Nov 2021 19:40

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