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A One-Pot Azido Reductive Tandem Mono-N-Alkylation Employing Dialkylboron Triflates: Online ESI-MS Mechanistic Investigation

Nagula Shankaraiah, Nagula Markandeya, Vunnam Srinivasulu, Kokkonda Sreekanth, Ch. Sanjeeva Reddy*, Leonardo S. Santos and Ahmed Kamal*

*Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 607, India, Email: ahmedkamaliict.res.in, chsrkucyahoo.co.in

N. Shankaraiah, N. Markandeya, V. Srinivasulu, K. Sreekanth, C. S. Reddy, L. S. Santos, A. Kamal, J. Org. Chem., 2011, 76, 7017-7026.

DOI: 10.1021/jo200931m (free Supporting Information)



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Abstract

An efficient, environmentally benign and practical one-pot reductive tandem mono-N-alkylation of both aromatic and aliphatic azides using dialkylboron triflates as alkylating agents enables 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-cyclization process.

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proposed mechanism



Key Words

Amines


ID: J42-Y2011-2400