- Reaction of 1-Iodoalkynes with Tin Metal: A New Approach to the Sn–C sp Bond Formation
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Abstract: Tin iodoalkynylides were synthesized by the reaction of 1-iodoalkynes with tin metal. The scope of the reaction and the composition of the resulting mixtures were studied. The formation of tin iodoalkynylides was confirmed by counter synthesis v
- Chikava, A. R.,Konshin, V. V.,Levashov, A. S.
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- Tetraalkynylstannanes in the Stille cross coupling reaction: a new effective approach to arylalkynes
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The Stille-type cross coupling reaction with tetraalkynylstannanes was studied in detail for the first time. The reaction provides a simple and effective route towards a variety of arylalkynes. The advantages and limitations of the proposed procedure are discussed.
- Levashov, Andrey S.,Buryi, Dmitrii S.,Goncharova, Olga V.,Konshin, Valeriy V.,Dotsenko, Victor V.,Andreev, Alexey A.
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supporting information
p. 2910 - 2918
(2017/04/14)
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- A reaction of tin tetra(N,N-diethylcarbamate) with phenylacetylene as a new route to tetra(phenylethynyl)tin
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A reaction of tin tetra(N,N-diethylcarbamate) with phenylacetylene afforded tetra-(phenylethynyl)tin in 77% yield. The reaction can be promoted by Lewis acids.
- Levashov,Andreev,Buryi,Konshin
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p. 775 - 776
(2015/01/30)
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- Organosubstituted 1,1'-Spirobisiloles and 1,1'-Spirobigermoles by Fourfold Organoboration of Tetra-1-alkynylsilanes and -germanes
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Si(CCR)4 R)4 nonatetraenes via the mono- and bisethyloboration compounds 3 or 4 (e.g. 3b, 4c) with different rates: Ge >> Si; Me > Ph.For comparison, compounds Sn(CR)4 react with Et3B in the absence of a solvent to mixtures of various spirotin compounds (5f, 5g, 6f, 8f, 9g, 10g, 11g) of which only 9g (R = Ph) corresponds to the spirosilanes and -germanes.This is the result of effective competition between intramolecular and intermolecular organoboration in the case of the tetra-1-alkynyltin compounds.The protodeborylation of 1a, b and 2d, e with MeCO2H leads to 12a, b and 13d, e, respectively. 12a isomerises by UV irradiation to allyl isomers 12a'.From 12a with 2 equiv. of maleic anhydride the 1:2 addition compound 14a is obtained, the autaddition of 12a, d leads to 15a, d.Spiro compound 12a reacts with (OC)5Fe or CpCo(C2H4)2 to give the cyclodiastereomeric η4-complexes 2-12a (16a1-a4; X-ray structure analysis of meso-16a1), (OC)3Fe-12a (17a) and (CpCo)2-12a (18a1-a4). - All products were characterized by multinuclear NMR, including measurements of the coupling constants 1J(13C13C), 2J(29Si29Si), nJ(29Si13C) and nJ(119Sn13C). Key Words: Silanes, tetra-1-alkynyl- / Germanes, tetra-1-alkynyl- / 1,1-Ethyloboration, intermolecular / 1,1-Vinyloboration, intramolecular / Spirosilanes / Spirogermanes / Protodeborylation / Transition metals, η4-complexes of
- Koester, Roland,Seidel, Guenter,Klopp, Ingo,Krueger, Carl,Kehr, Gerald,et al.
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p. 1385 - 1396
(2007/10/02)
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- Direct Formation of Reactive Alkynyltrichlorotins from 1-Alkynes, SnCl4, and Bu3N. A Mild Alkynylation Reagent of Aldehydes, Acetals, and Enones
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A reagent system of 1-alkyne, SnCl4, and Bu3N alkynylates aldehydes, acetals,and enones under mild reaction conditions giving acetylenic alcohols, acetylenic ethers, and acetylenic ketones, respectively, in high yields.Alkynyltrichlorotins are shown to be
- Yamaguchi, Masahiko,Hayashi, Akio,Hirama, Masahiro
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p. 2479 - 2482
(2007/10/02)
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