- Chemoselective Synthesis of 1,1-Disubstituted Vinyl Triflates from Terminal Alkynes Using TfOH in the Presence of TMSN3
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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
- Tummatorn, Jumreang,Punjajom, Kunlayanee,Rodphon, Warabhorn,Ruengsangtongkul, Sureeporn,Chaisan, Nattawadee,Lumyong, Kanyapat,Thongsornkleeb, Charnsak,Nimnual, Phongprapan,Ruchirawat, Somsak
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supporting information
p. 4694 - 4697
(2019/06/27)
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- Radical Desulfur-Fragmentation and Reconstruction of Enol Triflates: Facile Access to α-Trifluoromethyl Ketones
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We report an efficient oxidative radical desulfur-fragmentation and reconstruction of enol triflates for the synthesis of α-CF3ketones. Preliminary mechanistic studies disclosed that oxidative fragmentation to release a CF3radical fr
- Su, Xiaolong,Huang, Honggui,Yuan, Yaofeng,Li, Yi
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supporting information
p. 1338 - 1341
(2017/01/24)
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- Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates
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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.
- Cai, Guilong,Zhou, Zhibing,Wu, Wenchao,Yao, Bo,Zhang, Shaowen,Li, Xiaofang
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supporting information
p. 8702 - 8706
(2016/10/03)
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- Continuous flow α-trifluoromethylation of ketones by metal-free visible light photoredox catalysis
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A continuous-flow, two-step procedure for the preparation of α-CF3-substituted carbonyl compounds has been developed. The carbonyl substrates were converted in situ into the corresponding silyl enol ethers, mixed with the CF3 radical source, and then irradiated with visible light using a flow reactor based on transparent tubing and a household compact fluorescent lamp. The continuous protocol uses Eosin Y as an inexpensive photoredox catalyst and requires only 20 min to complete the two reaction steps.
- Cantillo, David,De Frutos, Oscar,Rincon, Juan A,Mateos, Carlos,Kappe, C. Oliver
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supporting information
p. 896 - 899
(2014/03/21)
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- Cationic gold(I) π-complexes of terminal alkynes and their conversion to dinuclear σ,π-acetylide complexes
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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.
- Brown, Timothy J.,Widenhoefer, Ross A.
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scheme or table
p. 6003 - 6009
(2012/01/14)
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