Domino Pd 0 ‐Catalyzed C(sp 3 )–H Arylation/Electrocyclic Reactions via Benzazetidine Intermediates | Zendy

Rocaboy Ronan | Zendy; Dailler David | Zendy; Zellweger Florian | Zendy; Neuburger Markus | Zendy; Salomé Christophe | Zendy; Clot Eric | Zendy; Baudoin Olivier | Zendy

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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.

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