4.8 Article

Acetohydrazone: A Transient Directing Group for Arylation of Unactivated C(sp3)-H Bonds

Journal

ORGANIC LETTERS
Volume 18, Issue 11, Pages 2708-2711

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01170

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Funding

  1. National Natural Science Foundation of China [81273397, 81561148011]
  2. Chinese National Science & Technology Major Project Key New Drug Creation and Manufacturing Program [2013ZX09508104]

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A straightforward and efficient method has been developed for the synthesis of 2-benzylbenzaldehyde derivatives from 2-methylbenzaldehyde and iodobenzene via a C(sp(3))-H activation process. In the course of the activation reaction, acetohydrazone is formed between 2-benzylbenzaldehyde and acetohydrazine as a transient directing group. As a new kind of transient directing group, acetohydrazone exhibits a remarkable directing effect to give corresponding products in good to excellent yields.

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