Jump to main content
Jump to site search

Issue 37, 2016
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Article information


Submitted
13 Jul 2016
Accepted
18 Aug 2016
First published
18 Aug 2016

Org. Biomol. Chem., 2016,14, 8702-8706
Article type
Paper

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

G. Cai, Z. Zhou, W. Wu, B. Yao, S. Zhang and X. Li, Org. Biomol. Chem., 2016, 14, 8702
DOI: 10.1039/C6OB01765G

Social activity

Search articles by author

Spotlight

Advertisements