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1.
Angew Chem Int Ed Engl ; 63(18): e202401671, 2024 Apr 24.
Article in English | MEDLINE | ID: mdl-38418423

ABSTRACT

The rapid assembly of valuable cyclic amine architectures in a single step from simple precursors has been recognized as an ideal platform in term of efficiency and sustainability. Although a vast number of studies regarding cyclic amine synthesis has been reported, new synthetic disconnection approaches are still high in demand. Herein, we report a catalytic radical-polar crossover cycloaddition to cyclic amine synthesis triggered from primary sulfonamide under photoredox condition. This newly developed disconnection, comparable to established synthetic approaches, will allow to construct ß, ß-disubstituted cyclic amine and ß-monosubstituted cyclic amine derivatives efficiently. This study highlights the unique utility of primary sulfonamide as a bifunctional reagent, which acts as a radical precursor and a nucleophile. The open-shell methodology demonstrates broad tolerance to various functional groups, drug derivatives and natural products in an economically and sustainable fashion.

2.
Chem Asian J ; 17(23): e202200858, 2022 Dec 01.
Article in English | MEDLINE | ID: mdl-36136743

ABSTRACT

A novel approach towards the efficient assembly of ß-fluoroalkylated arenes is presented here based on Pd/norbornene cooperative catalysis, which features an excellent functional group tolerance, as well as a broad ipso termination scope. The mild reaction conditions enabled the diversity-oriented synthesis (DOS) of the 13 and 14-membered fluorinated macrolactones which is extremely challenging otherwise. This new abstract could be used instead of our old version.


Subject(s)
Norbornanes , Palladium , Catalysis
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