Journal
TETRAHEDRON LETTERS
Volume 56, Issue 11, Pages 1423-1426Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.01.175
Keywords
DIAD; Cu catalysis; C-H cyclization; Alkene; Cyanomethylation
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Funding
- National Natural Science Foundation of China [21462017, 21372251]
- China Postdoctoral Science Foundation [2014M560649]
- Scientific Research Fund of Hunan Provincial Education Department [13B094]
- fund of Science and Technology Innovation and Entrepreneur for Hunan Young Talents
- Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry
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A novel and practical DIAD-promoted oxidative cyanomethylation of alkenes with acetonitrile by copper catalysis was developed, in which oxindoles bearing a nitrile moiety at the 3-position were synthesized efficiently via dual C-H bond cleavage of an arene and acetonitrile. This protocol demonstrated that DIAD served as a new promoter instead of commonly encountered AgF or base for the C-sp3-H functionalization of acetonitrile for the first time. (C) 2015 Elsevier Ltd. All rights reserved.
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