1344025-28-0Relevant articles and documents
Chemoselective Synthesis of 1,1-Disubstituted Vinyl Triflates from Terminal Alkynes Using TfOH in the Presence of TMSN3
Tummatorn, Jumreang,Punjajom, Kunlayanee,Rodphon, Warabhorn,Ruengsangtongkul, Sureeporn,Chaisan, Nattawadee,Lumyong, Kanyapat,Thongsornkleeb, Charnsak,Nimnual, Phongprapan,Ruchirawat, Somsak
supporting information, p. 4694 - 4697 (2019/06/27)
1,1-Disubstituted vinyl triflates are synthesized by direct hydrotriflation of terminal alkynes employing a combination of TfOH and TMSN3 in DCM at room temperature. Interestingly, under these conditions, only terminal alkynes were selectively
Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates
Cai, Guilong,Zhou, Zhibing,Wu, Wenchao,Yao, Bo,Zhang, Shaowen,Li, Xiaofang
supporting information, p. 8702 - 8706 (2016/10/03)
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.
Cationic gold(I) π-complexes of terminal alkynes and their conversion to dinuclear σ,π-acetylide complexes
Brown, Timothy J.,Widenhoefer, Ross A.
scheme or table, p. 6003 - 6009 (2012/01/14)
Treatment of a suspension of (IPr)AuCl [IPr = 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene] and AgSbF6 with terminal arylacetylenes led to the formation of thermally unstable gold π-alkyne complexes of the form [(IPr)Au(η 2-HC≡ CAr)]+SbF 6 - in ≥86 ± 5% yield, which were characterized by spectroscopy without isolation. Warming these complexes to 0 °C led to C(sp)-H bond cleavage and formation of dinuclear gold(I) σ,π-acetylide complexes of the form {[(IPr)Au]2(η 1,η 2-C≡ CAr)}+SbF6 -, three of which were isolated in 99% yield and one of which was characterized by X-ray crystallography. 1H NMR analysis of the conversion of gold π-arylacetylene complexes to σ,π-acetylide complexes established protonation of free arylacetylene, indicating the generation of a strong Bronsted acid under reaction conditions.
