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Development of a simple system for the oxidation of electron-rich diazo compounds to ketones

O’Connor, Nicholas R. and Bolgar, Peter and Stoltz, Brian M. (2016) Development of a simple system for the oxidation of electron-rich diazo compounds to ketones. Tetrahedron Letters, 57 (8). pp. 849-851. ISSN 0040-4039. http://resolver.caltech.edu/CaltechAUTHORS:20160201-141332316

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Abstract

Mild heating of diazo compounds in DMSO furnishes ketone products in moderate to excellent yields. The reaction is particularly effective on electron-rich substrates and exhibits high chemoselectivity, allowing for the use of diazo compounds containing additional oxidation-prone functional groups. This straightforward protocol offers an alternate route to synthetically useful ɑ-ketoesters from readily available aryl diazoacetates.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/j.tetlet.2016.01.020DOIArticle
http://www.sciencedirect.com/science/article/pii/S004040391630020XPublisherArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2016 Elsevier Ltd. Received 7 December 2015, Revised 5 January 2016, Accepted 6 January 2016, Available online 8 January 2016. The authors wish to thank the NSF (CHE-1265591), Amgen, and Caltech for financial support. P.B. is grateful to St Catharine’s College (University of Cambridge) and the Haller US Travel Fund for their support of an undergraduate summer research exchange program. Dr. David VanderVelde (NMR), Dr. Mona Shahgholi (HRMS), and Shoshana Bachman (ATR-IR) are thanked for assistance with characterization.
Funders:
Funding AgencyGrant Number
NSFCHE-1265591
AmgenUNSPECIFIED
CaltechUNSPECIFIED
St Catharine’s College, Cambridge UNSPECIFIED
Haller US Travel FundUNSPECIFIED
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
Subject Keywords:Oxidation; Diazo compounds; Ketones; Dimethyl sulfoxide; Chemoselective transformation
Record Number:CaltechAUTHORS:20160201-141332316
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160201-141332316
Official Citation:Nicholas R. O’Connor, Peter Bolgar, Brian M. Stoltz, Development of a simple system for the oxidation of electron-rich diazo compounds to ketones, Tetrahedron Letters, Volume 57, Issue 8, 24 February 2016, Pages 849-851, ISSN 0040-4039, http://dx.doi.org/10.1016/j.tetlet.2016.01.020. (http://www.sciencedirect.com/science/article/pii/S004040391630020X)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:64138
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:01 Feb 2016 23:33
Last Modified:10 Jul 2017 23:50

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