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Carbon dioxide: A reagent for the protection of nucleophilic centers and the simultaneous activation of alternative locations to electrophilic attack: 15. A synthetic method for the α‐substitution of N ‐phenylbenzylamine
Author(s) -
Katritzky A. R.,
Akutagawa K.,
Fan WeiQiang
Publication year - 1989
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19890070515
Subject(s) - chemistry , electrophile , decarboxylation , reagent , carbamate , lithium (medication) , electrophilic substitution , nucleophile , nucleophilic substitution , carbon atom , carbon fibers , carbon dioxide , medicinal chemistry , substitution reaction , butyllithium , organic chemistry , combinatorial chemistry , catalysis , ring (chemistry) , medicine , materials science , composite number , composite material , endocrinology
N ‐Phenylbenzylamine has been converted into a variety of α‐substituted derivatives in one‐pot sequences, using carbon dioxide both for N ‐protection and α‐carbon activation, and then subsequent lithiation at the α‐carbon atom by either tert ‐ or n ‐butyllithium. The resulting lithium carbamate reacts with electrophiles, followed smooth acid‐catalyzed decarboxylation under mild condition to give α‐substituted N ‐phenylbenzylamines in good yields.