Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflatesElectronic supplementary information (ESI) available: Experimental details, compound characterization, copies of 1H NMR and 13C NMR spectra. See DOI: 10.1039/c6ob01765g

• Main Authors: Cai, Guilong, Zhou, Zhibing, Wu, Wenchao, Yao, Bo, Zhang, Shaowen, Li, Xiaofang
• Format: Journal Article
• Published: 21.09.2016
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c6ob01765g

Pd-Catalyzed C(sp 3 )-C(sp 2 ) cross-coupling of Y(CH 2 SiMe 3 ) 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(PPh 3 ) 4 or Pd(PPh 3 ) 2 Cl 2 , 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. The Pd-catalyzed cross-coupling with the Hosomi-Sakurai reaction led to a novel three-component reaction using Y(CH 2 SiMe 3 ) 3 (THF) 2 as a nucleophilic one-carbon synthon.