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Tunable Hydride Transfer in the Redox Amination of Indoline with Aldehyde: An Attractive Intramolecular Hydrogen‐Bond Effect
Author(s) -
Mao Hui,
Xu Runsheng,
Wan Jieping,
Jiang Zhengyang,
Sun Cuirong,
Pan Yuanjiang
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001896
Subject(s) - indoline , intramolecular force , chemistry , hydride , aldehyde , amination , reductive amination , redox , hydrogen bond , dehydrogenation , photochemistry , organic chemistry , hydrogen , catalysis , molecule
Hydride hijacked by “hydrogen”! N ‐Alkylindoles and N ‐alkylindolines were obtained in the redox amination of indoline with aldehyde, which was tuned by a hydrogen‐bond effect. Salicylaldehyde gave the indoline‐type product via intermolecular hydride transfer, while other aromatic aldehydes gave the indole‐type product via intramolecular hydride transfer.