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Synthesis of Aryl Ketoamides via Aryne Insertion into Imides

Wright, Austin C. and Haley, Christopher K. and Lapointe, Guillaume and Stoltz, Brian M. (2016) Synthesis of Aryl Ketoamides via Aryne Insertion into Imides. Organic Letters, 18 (12). pp. 2793-2795. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20160609-145221780

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Abstract

An insertion of arenes into both imides and anhydrides via reactive aryne intermediates is presented. The reaction is performed under exceptionally mild conditions, and the corresponding ketoamide products are amenable to derivatization to deliver a variety of synthetically useful motifs such as quinolones, indoles, and ketoanilines.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/acs.orglett.6b00994DOIArticle
http://pubs.acs.org/doi/abs/10.1021%2Facs.orglett.6b00994PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.6b00994PublisherSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2016 American Chemical Society. Publication Date (Web): June 7, 2016. The authors thank the NSF (CCE 1265591), Caltech, and Amgen for financial support. G.L. is grateful to the Swiss National Science Foundation (SNSF) for a postdoctoral fellowship. Dr. Scott C. Virgil (Caltech) is thanked for assistance with compound isolation. Dr. Mona Shahgholi (Caltech) is acknowledged for help in structural determination and characterizations. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NSFCCE-1265591
CaltechUNSPECIFIED
AmgenUNSPECIFIED
Swiss National Science Foundation (SNSF)UNSPECIFIED
Issue or Number:12
Record Number:CaltechAUTHORS:20160609-145221780
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160609-145221780
Official Citation:Synthesis of Aryl Ketoamides via Aryne Insertion into Imides Austin C. Wright, Christopher K. Haley, Guillaume Lapointe, and Brian M. Stoltz Organic Letters 2016 18 (12), 2793-2795 DOI: 10.1021/acs.orglett.6b00994
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:67803
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:10 Jun 2016 18:54
Last Modified:03 Oct 2019 10:08

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