Mechanistic Insights into the Palladium-Catalyzed Domino Synthesis of 10,11-Dihydro-5H-dibenzo[b,e][1,4]diazepines

作者：Laha Joydev K^*; Tummalapalli K S Satyanarayana; Gupta Ankur

来源：European Journal of Organic Chemistry, 2014, 2014(22): 4773-4779.

DOI：10.1002/ejoc.201402207

• Domino reactions
• Nitrogen heterocycles
• Cyclization
• Palladium
• Homogeneous catalysis

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.

• 出版日期2014-8