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The First OCCCO Pentadentate Chelates: Osmium Mediated Stepwise Oxidations of Terminal Alkynes by Pyridine N ‐Oxide
Author(s) -
Lin Jianfeng,
Xu Qiannan,
Lin Xinlei,
Hua Yuhui,
Chen Dafa,
Ruan Yonghong,
Zhang Hong,
Xia Haiping
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000227
Subject(s) - chemistry , osmium , ruthenium , pyridine , chelation , rhodium , aldehyde , alkyne , oxide , catalysis , combinatorial chemistry , metal , medicinal chemistry , photochemistry , organic chemistry
Summary of main observation and conclusion Oxygen atom transfer reactions between alkynes and heteroarene N ‐oxides are currently mediated by transition metal, such as gold, ruthenium or rhodium, but they have never been catalyzed by osmium. Herein, we report stepwise oxidations of terminal alkynes mediated by an osmium carbolong complex, using pyridine N ‐oxide as the oxidant, yielding novel aldehyde‐ or carboxylic acid‐coordinated osmapentalyne derivatives selectively. The mechanism was illustrated by density functional theory calculations, providing a new route for oxygen atom transfer between heteroarene N ‐oxides and alkynes.