Fe-promoted cross coupling of homobenzylic methyl ethers with Grignard reagents via sp3 C–O bond cleavage

Shuang Luo; Da-Gang Yu; Ru-Yi Zhu; Xin Wang; Lei Wang; Zhang-Jie Shi

doi:10.1039/C3CC43616K

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Fe-promoted cross coupling of homobenzylic methyl ethers with Grignard reagentsvia sp³ C–O bond cleavage†

Shuang Luo,‡^a Da-Gang Yu,‡^a Ru-Yi Zhu,^a Xin Wang,^b Lei Wang^b and Zhang-Jie Shi*^ac

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* Corresponding authors

^a Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Green Chemistry Center, Peking University, Beijing 100871, China
E-mail: zshi@pku.edu.cn
Fax: +86 10-6276-0890
Tel: +86 10-6276-0890

^b Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China

^c State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Abstract

The first iron-catalyzed formal cross coupling of homobenzylic methyl ethers with alkyl Grignard reagents is realized. The reaction is proposed to proceed through a sequence of dehydroalkoxylation to form the vinyl-intermediate, followed by Fe-catalyzed selective carbometalation to form a benzylic Grignard reagent.

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Article information

DOI: https://doi.org/10.1039/C3CC43616K
Article type: Communication
Submitted: 14 May 2013
Accepted: 02 Jul 2013
First published: 02 Jul 2013

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Chem. Commun., 2013,49, 7794-7796

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Fe-promoted cross coupling of homobenzylic methyl ethers with Grignard reagents via sp³ C–O bond cleavage

S. Luo, D. Yu, R. Zhu, X. Wang, L. Wang and Z. Shi, Chem. Commun., 2013, 49, 7794 DOI: 10.1039/C3CC43616K

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