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Electrochemical Oxidative C(sp 3 )−H/N−H Cross‐Coupling for N ‐Mannich Bases with Hydrogen Evolution
Author(s) -
Wang Pan,
Yang Zhenlin,
Wu Ting,
Xu Chenyang,
Wang Ziwei,
Lei Aiwen
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201802676
Subject(s) - chemistry , electrochemistry , succinimides , heteroatom , kinetic isotope effect , bond cleavage , molecule , hydrogen bond , medicinal chemistry , stereochemistry , organic chemistry , catalysis , deuterium , ring (chemistry) , physics , electrode , quantum mechanics
N ‐Mannich bases are an important structure in various functional molecules. A new protocol to synthesize N ‐Mannich bases was established through electrochemical external‐oxidant‐free C(sp 3 )−H/N−H cross‐coupling with hydrogen evolution. Various N ‐methylanilines were explored in this transformation. Moreover, simple amides, heteroatom‐containing amides, and succinimides were well tolerated in moderate‐to‐good yields. In addition, the electrochemical dehydrogenative C(sp 3 )−H/N−H cross‐coupling could be scaled up to 5 mmol. By using triethyl phosphite as trapping agent, the phosphorylation product was detected. At the same time, kinetic isotope effect experiments showed that the cleavage of the C−H bond is the rate‐limiting step.