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. 2016 Jun 3;18(11):2708-11.
doi: 10.1021/acs.orglett.6b01170. Epub 2016 May 19.

Acetohydrazone: A Transient Directing Group for Arylation of Unactivated C(sp(3))-H Bonds

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Acetohydrazone: A Transient Directing Group for Arylation of Unactivated C(sp(3))-H Bonds

Fei Ma et al. Org Lett. .

Abstract

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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