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Domino Pd 0 ‐Catalyzed C(sp 3 )–H Arylation/Electrocyclic Reactions via Benzazetidine Intermediates
Author(s) -
Rocaboy Ronan,
Dailler David,
Zellweger Florian,
Neuburger Markus,
Salomé Christophe,
Clot Eric,
Baudoin Olivier
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807097
Subject(s) - chemistry , catalysis , electrocyclic reaction , amide , nitrogen atom , ring (chemistry) , domino , medicinal chemistry , reaction intermediate , reactive intermediate , photochemistry , organic chemistry
The Pd 0 ‐catalyzed C(sp 3 )‐H arylation of 2‐bromo‐N‐methylanilides leads to unstable benzazetidine intermediates that rearrange to benzoxazines through 4π electrocyclic ring‐opening and 6π electrocyclization. The introduction of a bulky, non‐activatable amide group on the nitrogen atom was key to favor the challenging reductive elimination step and disfavor undesired reaction pathways.