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Please use this identifier to cite or link to this item: http://dspace.utalca.cl/handle/1950/8776

Title: A One-Pot Azido Reductive Tandem Mono-N-Alkylation Employing Dialkylboron Triflates: Online ESI-MS Mechanistic Investigation
Authors: Shankaraiah, N.
Markandeya, N.
Srinivasulu, V.
Sreekanth, K.
Kamal, A.
Santos, L.S.
Reddy, C.S.
Keywords: general stereospecific synthesis
Issue Date: Sep-2011
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY Volume: 76 Issue: 17 Pages: 7017-7026 DOI: 10.1021/jo200931m
Abstract: An efficient one-pot reductive tandem mono-N-alkylation of both aromatic and aliphatic azides using diallcylboron triflates as allcylating agents has been examined under standardized reaction conditions. This methodology after optimization has been employed toward the syntheses of various secondary alkyl as well as aryl amines, including the synthesis of N10-butylated pyrrolo [2,1-c] [1,4]benzodiazepine-5,11-diones via in situ azido reductive-cydization process. This protocol is particularly attractive to provide an environmentally benign and practical method for mono-N-alkylation from organic azides without the use of toxic catalysts or corrosive alkylating agents. In addition, the mechanistic aspects have been investigated and the intermediates associated with this selective transformation have been intercepted and characterized by online monitoring of the reaction by ESI-MS/MS.
Description: Santos, LS (Santos, Leonardo S.)Univ Talca, Chem Inst Nat Resources, Lab Asymmetr Synth, Talca, Chile
URI: http://dspace.utalca.cl/handle/1950/8776
ISSN: 0022-3263
Appears in Collections:Artículos en publicaciones ISI - Universidad de Talca

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