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

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Summary

Introduction

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.

Results
Conclusion

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