Methylation of C(sp3)-H/C(sp2)-H bonds with methanol catalyzed by cobalt system

Zhenghui Liu; Zhenzhen Yang; Xiaoxiao Yu; Hongye Zhang; Bo Yu; Yanfei Zhao; Zhimin Liu

doi:10.1021/acs.orglett.7b02462

Methylation of C(sp³)-H/C(sp²)-H bonds with methanol catalyzed by cobalt system

Zhenghui Liu, Zhenzhen Yang, Xiaoxiao Yu, Hongye Zhang, Bo Yu, Yanfei Zhao, Zhimin Liu

Research output: Contribution to journal › Article › peer-review

102 Scopus citations

Abstract

A highly efficient Co-based catalytic system, composed of a commercially available Co salt, a tetradentate phosphine ligand P-(CH₂CH₂PPh₂)₃(PP₃), and a base (denoted as [Co]/PP₃/base), is developed for the methylation of C(sp³)-H and C(sp²)-H bonds using methanol as a methylating reagent. The Co(BF₄)₂.6H₂O/PP₃/K₂CO₃ catalytic system showed high catalytic activity for the methylation of C-H bonds in aryl alkyl ketones, aryl acetonitriles, and indoles, with wide substrate scope and good functional group tolerance, and methylsubstituted products were obtained in good to excellent yields at 100 °C. This cheap, readily available, and highly efficient Co-based catalytic system may have promising applications in methylation reaction using methanol.

Original language	English
Pages (from-to)	5228-5231
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.7b02462
State	Published - Oct 6 2017
Externally published	Yes

Funding

We thank the National Natural Science Foundation of China (Nos. 21673256, 21402208, 21403252, and 21503239).

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10.1021/acs.orglett.7b02462

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title = "Methylation of C(sp3)-H/C(sp2)-H bonds with methanol catalyzed by cobalt system",

abstract = "A highly efficient Co-based catalytic system, composed of a commercially available Co salt, a tetradentate phosphine ligand P-(CH2CH2PPh2)3(PP3), and a base (denoted as [Co]/PP3/base), is developed for the methylation of C(sp3)-H and C(sp2)-H bonds using methanol as a methylating reagent. The Co(BF4)2.6H2O/PP3/K2CO3 catalytic system showed high catalytic activity for the methylation of C-H bonds in aryl alkyl ketones, aryl acetonitriles, and indoles, with wide substrate scope and good functional group tolerance, and methylsubstituted products were obtained in good to excellent yields at 100 °C. This cheap, readily available, and highly efficient Co-based catalytic system may have promising applications in methylation reaction using methanol.",

author = "Zhenghui Liu and Zhenzhen Yang and Xiaoxiao Yu and Hongye Zhang and Bo Yu and Yanfei Zhao and Zhimin Liu",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b02462",

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T1 - Methylation of C(sp3)-H/C(sp2)-H bonds with methanol catalyzed by cobalt system

AU - Liu, Zhenghui

AU - Yang, Zhenzhen

AU - Yu, Xiaoxiao

AU - Zhang, Hongye

AU - Yu, Bo

AU - Zhao, Yanfei

AU - Liu, Zhimin

PY - 2017/10/6

Y1 - 2017/10/6

N2 - A highly efficient Co-based catalytic system, composed of a commercially available Co salt, a tetradentate phosphine ligand P-(CH2CH2PPh2)3(PP3), and a base (denoted as [Co]/PP3/base), is developed for the methylation of C(sp3)-H and C(sp2)-H bonds using methanol as a methylating reagent. The Co(BF4)2.6H2O/PP3/K2CO3 catalytic system showed high catalytic activity for the methylation of C-H bonds in aryl alkyl ketones, aryl acetonitriles, and indoles, with wide substrate scope and good functional group tolerance, and methylsubstituted products were obtained in good to excellent yields at 100 °C. This cheap, readily available, and highly efficient Co-based catalytic system may have promising applications in methylation reaction using methanol.

AB - A highly efficient Co-based catalytic system, composed of a commercially available Co salt, a tetradentate phosphine ligand P-(CH2CH2PPh2)3(PP3), and a base (denoted as [Co]/PP3/base), is developed for the methylation of C(sp3)-H and C(sp2)-H bonds using methanol as a methylating reagent. The Co(BF4)2.6H2O/PP3/K2CO3 catalytic system showed high catalytic activity for the methylation of C-H bonds in aryl alkyl ketones, aryl acetonitriles, and indoles, with wide substrate scope and good functional group tolerance, and methylsubstituted products were obtained in good to excellent yields at 100 °C. This cheap, readily available, and highly efficient Co-based catalytic system may have promising applications in methylation reaction using methanol.

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JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Methylation of C(sp³)-H/C(sp²)-H bonds with methanol catalyzed by cobalt system

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