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Visible‐Light‐Induced Decarboxylative Acylation of Pyridine N ‐Oxides with α‐Oxocarboxylic Acids Using Fluorescein Dimethylammonium as a Photocatalyst
Author(s) -
Hou Chuanfu,
Sun Shouneng,
Liu Ziqi,
Zhang Hui,
Liu Yue,
An Qi,
Zhao Jian,
Ma Junjie,
Sun Zhizhong,
Chu Wenyi
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100168
Subject(s) - chemistry , acylation , decarboxylation , catalysis , photocatalysis , pyridine , solvent , zwitterion , radical , fluorescein , organic chemistry , photochemistry , combinatorial chemistry , fluorescence , molecule , physics , quantum mechanics
Herein, the development of a visible‐light‐induced catalytic system to achieve the decarboxylative acylation of pyridine N ‐oxides with α‐oxocarboxylic acids, at room temperature and using the organic dye fluorescein dimethylammonium as a new type of photocatalyst, is reported. A series of 2‐arylacylpyridine N ‐oxides were selectively synthesized in moderate to good yields by controlling the polarity of the reaction solvent. The developed strategy was successfully applied in the synthesis of an important intermediate of the drug, acrivastine, on a gram scale. Notably, this is the first time that fluorescein dimethylammonium has been used to catalyze the Minisci‐type C−H decarboxylative acylation reaction. The mechanism of decarboxylative acylation was studied by capturing adducts of acyl radicals and 1,1‐diphenylethylene to confirm a radical mechanism. The disclosed catalytic system provides a green synthetic strategy for decarboxylative acylation without the use of additional oxidants or metal catalysts.