Mechanistic insights into the palladium-catalyzed domino synthesis of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines

Article abstract of DOI:10.1002/ejoc.201402207

A palladium-catalyzed domino approach to the synthesis of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines starting from o-phenylenediamines and 2-bromobenzyl bromides or tosylates has been developed. Mechanistic studies support the following domino sequence. Intermolecular mono-N-benzylation of the o-phenylenediamine through oxidative palladium insertion, primarily at the benzylic position of the 2-bromobenzyl bromide, is followed by intramolecular N′-arylation. The intramolecular N′-arylation is demonstrated to be facilitated by coordination of a remote auxiliary nitrogen atom to the palladium atom.

Full text of DOI:10.1002/ejoc.201402207

Eur. J. Org. Chem. 2014 · © WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 · ISSN 1099–0690
SUPPORTING INFORMATION
DOI: 10.1002/ejoc.201402207
Title: Mechanistic Insights into the Palladium-Catalyzed Domino Synthesis of 10,11-Dihydro-5H-
dibenzo[b,e][1,4]diazepines
Author(s): Joydev K. Laha,* K. S. Satyanarayana Tummalapalli, Ankur Gupta

Table of Contents
Copies of 1HNMR and 13C NMR spectra
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