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Nitridomanganese(V) Complexes: Design, Preparation, and Use as Nitrogen Atom-Transfer Reagents

Du Bois, J. and Tomooka, Craig S. and Hong, Jason and Carreira, Erick M. (1997) Nitridomanganese(V) Complexes: Design, Preparation, and Use as Nitrogen Atom-Transfer Reagents. Accounts of Chemical Research, 30 (9). pp. 364-372. ISSN 0001-4842. https://resolver.caltech.edu/CaltechAUTHORS:20171205-095237857

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Abstract

Oxidation of organic substrates by direct oxygen-atom transfer from transition-metal complexes is of fundamental importance and has been subject to intensive investigation. Highly selective methods for alkene epoxidation and dihydroxylation have been described and are commonly employed in synthesis. By contrast, significantly fewer reagents and protocols are available for the analogous nitrogen-atom-transfer process, despite the enormous potential utility of such methodology. Recent efforts by other groups to develop general olefin amination strategies have led to impressive advances in both metalcatalyzed hydroxyamination and aziridination. Our interest in this area has resulted in the preparation and characterization of novel nitridomanganese complexes which may be activated for nitrogen-atom transfer. Pivotal to the success of this research has been the development of new protocols for the construction of these manganese nitride (Mn≡N) reagents. These systems have proven to be versatile and effective aminating agents with different classes of olefins which include both silyl enol ethers and glycals (eq 1). The following account documents these findings and highlights the unique chemistry of these complexes as nitrogen-atom-transfer reagents.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/ar960222vDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ar960222vPublisherArticle
ORCID:
AuthorORCID
Du Bois, J.0000-0001-7847-1548
Carreira, Erick M.0000-0003-1472-490X
Additional Information:© 1997 American Chemical Society. Received March 21, 1997. Publication Date (Web): September 11, 1997. J.D.B. is grateful to the National Science Foundation for a predoctoral fellowship (1993−96). J.H. thanks Pfizer for the gracious award of a Pfizer Undergraduate Summer Fellowship (1996). We are greatly appreciative to Professor Harry Gray and Dr. Don Low for many enlightening discussions. This research has been supported by generous grants from the David and Lucille Packard Foundation, Sloan Foundation, NIH, NSF, Merck, Pfizer, Zeneca, Lilly, and Pharmacia-UpJohn.
Funders:
Funding AgencyGrant Number
NSF Predoctoral FellowshipUNSPECIFIED
Pfizer Undergraduate Summer FellowshipUNSPECIFIED
David and Lucille Packard FoundationUNSPECIFIED
Alfred P. Sloan FoundationUNSPECIFIED
NIHUNSPECIFIED
MerckUNSPECIFIED
PfizerUNSPECIFIED
ZenecaUNSPECIFIED
LillyUNSPECIFIED
Pharmacia-UpJohnUNSPECIFIED
Issue or Number:9
Record Number:CaltechAUTHORS:20171205-095237857
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20171205-095237857
Official Citation:Nitridomanganese(V) Complexes:  Design, Preparation, and Use as Nitrogen Atom-Transfer Reagents. J. Du Bois,Craig S. Tomooka,Jason Hong, and, and Erick M. Carreira. Accounts of Chemical Research 1997 30 (9), 364-372. DOI: 10.1021/ar960222v.
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:83689
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Dec 2017 05:04
Last Modified:09 Mar 2020 13:18

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