Abstract
A novel approach for the synthesis of tertiary propargylamines is achieved through a Cu(OAc)2-catalyzed multicomponent reaction of primary amines, formaldehyde, arylboronic acids and alkynes, where a combination of PBM and A(3)-coupling reactions is involved in this new multicomponent reaction.
Highlights
Synthesis of tertiary propargylamines via a rationally designed multicomponent reaction of primary amines, formaldehyde, arylboronic acids and alkynes†
A novel approach for the synthesis of tertiary propargylamines is achieved through a Cu(OAc)2-catalyzed multicomponent reaction of primary amines, formaldehyde, arylboronic acids and alkynes, where a combination of Petasis borono–Mannich (PBM) and A3-coupling reactions is involved in this new multicomponent reaction
The Petasis borono–Mannich (PBM) reaction of aldehydes, amines and boronic acids, developed by Petasis in 1993,8 has attracted considerable attention in the synthesis of diverse α-hydroxyl amines, α-amino acids and nitrogen-containing heterocycles.[9,10]. Realizing both amines and aldehydes are involved in A3-coupling and PBM reactions, and a secondary amine is generally preferable to a primary one in A3 reaction;[5,7] it is possible to develop a novel multicomponent reaction in which the secondary amines produced from PBM reaction could serve as the amine component in further A3-coupling to construct the final propargylamines
Summary
Synthesis of tertiary propargylamines via a rationally designed multicomponent reaction of primary amines, formaldehyde, arylboronic acids and alkynes†. A novel approach for the synthesis of tertiary propargylamines is achieved through a Cu(OAc)2-catalyzed multicomponent reaction of primary amines, formaldehyde, arylboronic acids and alkynes, where a combination of PBM and A3-coupling reactions is involved in this new multicomponent reaction.
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