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A General Acid‐Mediated Hydroaminomethylation of Unactivated Alkenes and Alkynes
Author(s) -
Kaiser Daniel,
Tona Veronica,
Gonçalves Carlos R.,
Shaaban Saad,
Oppedisano Alberto,
Maulide Nuno
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201906910
Subject(s) - hydroamination , regioselectivity , chemistry , functional group , amine gas treating , combinatorial chemistry , catalysis , domino , amination , organic chemistry , scope (computer science) , computer science , programming language , polymer
Abstract In comparison to the extensively studied metal‐catalyzed hydroamination reaction, hydroaminomethylation has received significantly less attention despite its considerable potential to streamline amine synthesis. State‐of‐the‐art protocols for hydroaminomethylation of alkenes rely largely on transition‐metal catalysis, enabling this transformation only under highly designed and controlled conditions. Here we report a broadly applicable, acid‐mediated approach to the hydroaminomethylation of unactivated alkenes and alkynes. This methodology employs cheap, readily available, and bench‐stable reactants and affords the desired amines with excellent functional group tolerance and impeccable regioselectivity. The broad scope of this transformation, as well as mechanistic investigations and in situ domino functionalization reactions are reported.