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

Fei Ma; Min Lei; Lihong Hu

doi:10.1021/acs.orglett.6b01170

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

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

Authors

Fei Ma¹, Min Lei², Lihong Hu^{1

2}

Affiliations

¹ Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology , Shanghai 200237, P. R. of China.
² State key Laboratory of Drug Research, Shanghai Institute of Materia Medica, University of Chinese Academy of Sciences, Chinese Academy of Sciences , Shanghai 201203, P. R. of China.

PMID: 27193865
DOI: 10.1021/acs.orglett.6b01170

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.

Publication types

Research Support, Non-U.S. Gov't