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Mechanistic Insights into the Palladium‐Catalyzed Domino Synthesis of 10,11‐Dihydro‐5 H ‐dibenzo[ b , e ][1,4]diazepines
Author(s) -
Laha Joydev K.,
Satyanarayana Tummalapalli K. S.,
Gupta Ankur
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402207
Subject(s) - chemistry , domino , palladium , intramolecular force , nitrogen atom , catalysis , bromide , intermolecular force , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , molecule , ring (chemistry)
A palladium‐catalyzed domino approach to the synthesis of 10,11‐dihydro‐5 H ‐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.