Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates

Guilong Cai; Zhibing Zhou; Wenchao Wu; Bo Yao; Shaowen Zhang; Xiaofang Li

doi:10.1039/c6ob01765g

Pd-Catalyzed C(sp³)-C(sp²) cross-coupling of Y(CH₂SiMe₃)₃(THF)₂ with vinyl bromides and triflates

Guilong Cai, Zhibing Zhou, Wenchao Wu, Bo Yao^*, Shaowen Zhang, Xiaofang Li

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

9 Citations (Scopus)

Abstract

Pd-Catalyzed C(sp³)-C(sp²) cross-coupling of Y(CH₂SiMe₃)₃(THF)₂ with vinyl bromides and triflates has been developed for efficient synthesis of various allyltrimethylsilanes. The cross-coupling reaction was conducted at room temperature with low catalyst loading of either Pd(PPh₃)₄ or Pd(PPh₃)₂Cl₂, and exhibited high efficiency and a broad substrate scope. In combination with the cross-coupling by the Lewis-acid catalyzed Hosomi-Sakurai reaction, a novel three-component one-pot cascade reaction was then accomplished to deliver homoallylic alcohols and ethers with high regioselectivity and diastereoselectivity. The three-component reaction defined the yttrium complex as a novel one-carbon synthon, which could either trigger bifunctionalization of alkenes or link two electrophiles and would find applications in organic synthesis.

Original language	English
Pages (from-to)	8702-8706
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	37
DOIs	https://doi.org/10.1039/c6ob01765g
Publication status	Published - 2016

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title = "Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates",

abstract = "Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates has been developed for efficient synthesis of various allyltrimethylsilanes. The cross-coupling reaction was conducted at room temperature with low catalyst loading of either Pd(PPh3)4 or Pd(PPh3)2Cl2, and exhibited high efficiency and a broad substrate scope. In combination with the cross-coupling by the Lewis-acid catalyzed Hosomi-Sakurai reaction, a novel three-component one-pot cascade reaction was then accomplished to deliver homoallylic alcohols and ethers with high regioselectivity and diastereoselectivity. The three-component reaction defined the yttrium complex as a novel one-carbon synthon, which could either trigger bifunctionalization of alkenes or link two electrophiles and would find applications in organic synthesis.",

author = "Guilong Cai and Zhibing Zhou and Wenchao Wu and Bo Yao and Shaowen Zhang and Xiaofang Li",

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doi = "10.1039/c6ob01765g",

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T1 - Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates

AU - Cai, Guilong

AU - Zhou, Zhibing

AU - Wu, Wenchao

AU - Yao, Bo

AU - Zhang, Shaowen

AU - Li, Xiaofang

PY - 2016

Y1 - 2016

N2 - Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates has been developed for efficient synthesis of various allyltrimethylsilanes. The cross-coupling reaction was conducted at room temperature with low catalyst loading of either Pd(PPh3)4 or Pd(PPh3)2Cl2, and exhibited high efficiency and a broad substrate scope. In combination with the cross-coupling by the Lewis-acid catalyzed Hosomi-Sakurai reaction, a novel three-component one-pot cascade reaction was then accomplished to deliver homoallylic alcohols and ethers with high regioselectivity and diastereoselectivity. The three-component reaction defined the yttrium complex as a novel one-carbon synthon, which could either trigger bifunctionalization of alkenes or link two electrophiles and would find applications in organic synthesis.

AB - Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates has been developed for efficient synthesis of various allyltrimethylsilanes. The cross-coupling reaction was conducted at room temperature with low catalyst loading of either Pd(PPh3)4 or Pd(PPh3)2Cl2, and exhibited high efficiency and a broad substrate scope. In combination with the cross-coupling by the Lewis-acid catalyzed Hosomi-Sakurai reaction, a novel three-component one-pot cascade reaction was then accomplished to deliver homoallylic alcohols and ethers with high regioselectivity and diastereoselectivity. The three-component reaction defined the yttrium complex as a novel one-carbon synthon, which could either trigger bifunctionalization of alkenes or link two electrophiles and would find applications in organic synthesis.

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DO - 10.1039/c6ob01765g

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JO - Organic and Biomolecular Chemistry

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ER -

Pd-Catalyzed C(sp³)-C(sp²) cross-coupling of Y(CH₂SiMe₃)₃(THF)₂ with vinyl bromides and triflates

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