Silver-Free Palladium-Catalyzed C(sp3)–H Arylation of Saturated Bicyclic Amine Scaffolds | Zendy

Charlotte E. Coomber | Zendy; Laure Benhamou | Zendy; DejanKrešimir Bučar | Zendy; Peter D. Smith | Zendy; Michael J. Porter | Zendy; Tom D. Sheppard | Zendy

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Silver-Free Palladium-Catalyzed C(sp³)–H Arylation of Saturated Bicyclic Amine Scaffolds

Author(s) -

Charlotte E. Coomber,

Laure Benhamou,

DejanKrešimir Bučar,

Peter D. Smith,

Michael J. Porter,

Tom D. Sheppard

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b02665

Subject(s) - palladium , bicyclic molecule , catalysis , amine gas treating , chemistry , medicinal chemistry , organic chemistry

Herein, we report a silver-free Pd(II)-catalyzed C(sp 3 )-H arylation of saturated bicyclic and tricyclic amine scaffolds. The reaction provides good yields using a range of aryl iodides and aryl bromides including functionalized examples bearing aldehydes, ketones, esters, free phenols, and heterocycles. The methodology has been applied to medicinally relevant scaffolds. Two of the intermediate palladium complexes in the catalytic cycle have been prepared and characterized, and a mechanism is proposed. Removal of the directing group proceeded with good yield under relatively mild conditions.

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