Nickel(0)-Catalyzed Inert C-O Bond Functionalization: Organo Rare-Earth Metal Complex as the Coupling Partner

Xiangqian Yan; Fanzhi Yang; Guilong Cai; Qingwei Meng; Xiaofang Li

doi:10.1021/acs.orglett.7b03753

Nickel(0)-Catalyzed Inert C-O Bond Functionalization: Organo Rare-Earth Metal Complex as the Coupling Partner

Xiangqian Yan
, Fanzhi Yang^*
, Guilong Cai
, Qingwei Meng
, Xiaofang Li

^*Corresponding author for this work

Beijing Institute of Technology

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

16 Citations (Scopus)

Abstract

An organo rare-earth metal complex has been employed as a highly efficient nucleophile in Ni(0)-catalyzed C-O bond functionalization. The optimized catalytic system which consists of Ni(cod)₂, PCy₃, and t-BuONa could smoothly convert 1 equiv of naphthyl ethers to alkylated naphthalene analogues with 0.4 equiv of Ln(CH₂SiMe₃)₃(THF)₂, delivering good to excellent yields. The reaction system could also activate the ArCH₂-O bond with mild base.

Original language	English
Pages (from-to)	624-627
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.7b03753
Publication status	Published - 2 Feb 2018
Externally published	Yes

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title = "Nickel(0)-Catalyzed Inert C-O Bond Functionalization: Organo Rare-Earth Metal Complex as the Coupling Partner",

abstract = "An organo rare-earth metal complex has been employed as a highly efficient nucleophile in Ni(0)-catalyzed C-O bond functionalization. The optimized catalytic system which consists of Ni(cod)2, PCy3, and t-BuONa could smoothly convert 1 equiv of naphthyl ethers to alkylated naphthalene analogues with 0.4 equiv of Ln(CH2SiMe3)3(THF)2, delivering good to excellent yields. The reaction system could also activate the ArCH2-O bond with mild base.",

author = "Xiangqian Yan and Fanzhi Yang and Guilong Cai and Qingwei Meng and Xiaofang Li",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b03753",

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T1 - Nickel(0)-Catalyzed Inert C-O Bond Functionalization

T2 - Organo Rare-Earth Metal Complex as the Coupling Partner

AU - Yan, Xiangqian

AU - Yang, Fanzhi

AU - Cai, Guilong

AU - Meng, Qingwei

AU - Li, Xiaofang

PY - 2018/2/2

Y1 - 2018/2/2

N2 - An organo rare-earth metal complex has been employed as a highly efficient nucleophile in Ni(0)-catalyzed C-O bond functionalization. The optimized catalytic system which consists of Ni(cod)2, PCy3, and t-BuONa could smoothly convert 1 equiv of naphthyl ethers to alkylated naphthalene analogues with 0.4 equiv of Ln(CH2SiMe3)3(THF)2, delivering good to excellent yields. The reaction system could also activate the ArCH2-O bond with mild base.

AB - An organo rare-earth metal complex has been employed as a highly efficient nucleophile in Ni(0)-catalyzed C-O bond functionalization. The optimized catalytic system which consists of Ni(cod)2, PCy3, and t-BuONa could smoothly convert 1 equiv of naphthyl ethers to alkylated naphthalene analogues with 0.4 equiv of Ln(CH2SiMe3)3(THF)2, delivering good to excellent yields. The reaction system could also activate the ArCH2-O bond with mild base.

UR - https://www.scopus.com/pages/publications/85041596994

U2 - 10.1021/acs.orglett.7b03753

DO - 10.1021/acs.orglett.7b03753

M3 - Article

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AN - SCOPUS:85041596994

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SP - 624

EP - 627

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Nickel(0)-Catalyzed Inert C-O Bond Functionalization: Organo Rare-Earth Metal Complex as the Coupling Partner

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