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Title: Palladium-catalyzed enantioselective (2-naphthyl)methylation of azaarylmethyl amines
Enantioenriched azaarylmethyl amine derivatives are useful building blocks in synthetic and medicinal chemistry. To access these valuable motifs, an enantioselective palladium-catalyzed benzylation of azaarylmethyl amine pronucleophiles is introduced. Of note, this is a rare application of asymmetric (2-naphthyl)methylation of pro-nucleophiles with high p K a values (p K a ≈ 34 in DMSO). Control experiments support the notion that the coordination of Li + to the azaaryl nitrogen plays a critical role in the substitution process. With this procedure, enantioenriched (2-naphthyl)methylene azaarylmethyl amines with a variety of azaaryl groups (pyridyl, pyrazine, quinoxaline and isoquinoline) and cyclic and acyclic amines are readily obtained with good yields and enantioselectivities up to 99%.  more » « less
Award ID(s):
1902509
PAR ID:
10348009
Author(s) / Creator(s):
; ; ; ; ;
Date Published:
Journal Name:
Organic Chemistry Frontiers
Volume:
9
Issue:
10
ISSN:
2052-4129
Page Range / eLocation ID:
2721 to 2727
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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