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Rapid Oxidation Indoles into 2‐Oxindoles Mediated by PIFA in Combination with n ‐Bu 4 NCl ⋅ H 2 O
Author(s) -
Liang Peng,
Zhao Hang,
Zhou Tingting,
Zeng Kaiyun,
Jiao Wei,
Pan Yang,
Liu Yazhou,
Fang Dongmei,
Ma Xiaofeng,
Shao Huawu
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.202100234
Subject(s) - chemistry , oxindole , yield (engineering) , benzene , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
We report the development of a rapid approach for directly converting indoles into 2‐oxindoles promoted by HOCl formed in situ from the combination of (bis(trifluoroacetoxy) iodo)benzene (PIFA) and n ‐Bu 4 NCl ⋅ H 2 O. The procedure is widely functional group tolerant and provides 2‐oxindoles in up to 95% yield within 5 min. The potential applications of the developed methodology are demonstrated by the gram‐scale preparation of 3‐methyl‐2‐oxindole ( 11 a ), the one‐pot two‐step syntheses of spiro‐oxindoles 26 a and 26 b , and the formal synthesis of (‐)‐folicanthine ( 2 ).
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