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A copper-catalyzed arylation of tryptamines for the direct synthesis of aryl pyrroloindolines

Kieffer, Madeleine E. and Chuang, Kangway V. and Reisman, Sarah E. (2012) A copper-catalyzed arylation of tryptamines for the direct synthesis of aryl pyrroloindolines. Chemical Science, 3 (11). pp. 3170-3174. ISSN 2041-6520. PMCID PMC3480223. doi:10.1039/c2sc20914d. https://resolver.caltech.edu/CaltechAUTHORS:20121213-102648677

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Abstract

An operationally simple, copper-catalyzed arylation of N-tosyltryptamines provides direct access to C3-aryl pyrroloindolines. A range of electron-donating and electron-withdrawing substituents is tolerated on both the indole backbone and the aryl electrophile. These reactions occur under ambient temperatures and with equimolar quantities of the coupling partners.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1039/c2sc20914d DOIArticle
http://pubs.rsc.org/en/Content/ArticleLanding/2012/SC/c2sc20914dPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3480223/PubMed CentralArticle
ORCID:
AuthorORCID
Chuang, Kangway V.0000-0002-0652-8071
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2012 The Royal Society of Chemistry. Received 9th July 2012, Accepted 9th August 2012. First published on the web 17 Aug 2012. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Sigma-Aldrich for a kind donation of chemicals. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, M.E.K, Grant no. DGE-1144469). Financial support from the California Institute of Technology and the NIH (NIGMS RGM097582A) is gratefully acknowledged.
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
CaltechUNSPECIFIED
NIHRGM097582A
Issue or Number:11
PubMed Central ID:PMC3480223
DOI:10.1039/c2sc20914d
Record Number:CaltechAUTHORS:20121213-102648677
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20121213-102648677
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:35975
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:17 Dec 2012 22:35
Last Modified:09 Nov 2021 23:19

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