53915-69-8Relevant academic research and scientific papers
PREPARATION OF α-ALLENIC AND β-ACETYLENIC ALCOHOLS BY TREATMENT OF A MIXTURE OF Bu3SnCH=C=CH2 AND RCHO WITH Bu2SnCl2 AND WATER
Boaretto, Andrea,Marton, Daniele,Tagliavini, Giuseppe
, p. 149 - 154 (1985)
Treatment of a mixture of Bu3SnCH=C=CH2 and RCHO (R = CH3, C2H5, (CH3)2CH, (CH3)3C) with Bu2SnCl2 in the presence of water gives isomeric mixtures of α-allenic and β-acetylenic alcohols with the α-allenic isomer predominating (ca. 75 percent).Reactions carried out without water give mixtures in which the isomeric ratio between the allenic and acetylenic alcohol varied between 70/30 and 50/50.In contrast β-acetylenic alcohols predominate when HCHO and α,β-unsaturated aldehydes (R = CH2CH, CH2=C(CH3), CH3CH=CH, C3H7CH=CH) are used.The stereochemical course of the reactions appear to depend upon the addition and isomerization rates of the Bu2Sn(CH2CCH)Cl intermediate.
Exploration of [2 + 2 + 2] cyclotrimerisation methodology to prepare tetrahydroisoquinoline-based compounds with potential aldo-keto reductase 1C3 target affinity
Santos, Ana R. N.,Sheldrake, Helen M.,Ibrahim, Ali I. M.,Danta, Chhanda Charan,Bonanni, Davide,Daga, Martina,Oliaro-Bosso, Simonetta,Boschi, Donatella,Lolli, Marco L.,Pors, Klaus
supporting information, p. 1476 - 1480 (2019/08/20)
Tetrahydroisoquinoline (THIQ) is a key structural component in many biologically active molecules including natural products and synthetic pharmaceuticals. Here, we report on the use of transition-metal mediated [2 + 2 + 2] cyclotrimerisation of alkynes to generate tricyclic THIQs with potential to selectively inhibit AKR1C3.
Indium(III) halide-catalyzed UV-irradiated radical coupling of iodomethylphosphorus compounds with various organostannanes
Suzuki, Itaru,Kiyokawa, Kensuke,Yasuda, Makoto,Baba, Akio
supporting information, p. 1728 - 1731 (2013/06/27)
The first catalytic radical coupling of iodomethylphosphorus compounds was accomplished with allyl-, alkenyl-, and allenylstannanes under UV irradiation in the presence of an indium(III) halide catalyst, for which a transmetalated allylic indium species was confirmed to be an active radical species.
Direct synthesis of alkynylstannanes: ZnBr2 catalyst for the reaction of tributyltin methoxide and terminal alkynes
Kiyokawa, Kensuke,Tachikake, Nodoka,Yasuda, Makoto,Baba, Akio
, p. 10393 - 10396 (2011/12/04)
Metal hopping: Various alkynylstannanes were synthesized by the direct reaction of Bu3SnOMe with terminal alkynes at room temperature in the presence of a ZnBr2 catalyst. Rather than acting as a Lewis acid, ZnBr2 was transmetalated with Bu3SnOMe to give Zn(OMe)2, which is key to the catalytic reaction. Copyright
A novel mode of access to polyfunctional organotin compounds and their reactivity in Stille cross-coupling reaction
Lamandé-Langle, Sandrine,Abarbri, Mohamed,Thibonnet, Jér?me,Duchêne, Alain
, p. 2368 - 2374 (2009/09/30)
Mono-, di-, tri- and tetra-functional organotin compounds were easily prepared in a sonicated Barbier reaction using ultrasound technology via coupling reaction of organo halides with tin halides (Bu3SnCl, Bu2SnCl2, BuSnCl
Convenient synthesis of alkenyl-, alkynyl-, and allenyl-substituted imidazo[1,2-a]pyridines via palladium-catalyzed cross-coupling reactions
Enguehard-Gueiffier, Cecile,Croix, Cecile,Hervet, Maud,Kazock, Jean-Yves,Gueiffier, Alain,Abarbri, Mohamed
, p. 2349 - 2367 (2008/03/29)
A systematic study on the Stille and Sonogashira cross-coupling of iodinated imidazo[1,2-a]pyridines was performed, permitting the preparation of various vinyl-, ethynyl-, and allenyl-substituted derivatives. These methods are particularly valuable, given their experimental simplicity and high degree of flexibility with regard to functional groups that can be introduced in positions 3, 6, or 8 of the imidazo[1,2-a]-pyridine core. Effects concerning different substitution positions and the nature of the 2-substituent under various reaction conditions are reported in detail for the above types of unsaturated groups introduced.
Double stannylation d'un sulfure propargylique par l'hydrure de tributyletain en presence de thiol
Lambert, Marie-Pierre,Ratier, Max,Duboudin, Jean-Georges,Petraud, Michel
, p. 181 - 188 (2007/10/02)
In the presence of small amounts of p-thiocresol, hydrostannylation of propargyl p-tolyl sulfide promotes the unexpected formation of (Z)-1,2-bis(organostannyl)olefin instead of yielding normal addition products.The application of a non-refocusing INEPT pulse sequence in 119Sn NMR spectroscopy allows the determination of its stereochemistry by comparison of observed patterns with calculated spectra.Key words: Hydrostannylation; Nuclear magnetic resonance; INEPT; Propargyl sulfides
Palladium-catalyzed coupling of stannyl allenes with aryl iodides
Aidhen,Braslau
, p. 789 - 797 (2007/10/02)
Substituted allenes are prepared by coupling stannyl allenes with aryl iodides under palladium(0) catalysis. A concise and versatile sequence starting from propargyl alcohols provides a route for the preparation of substituted allenes under extremely mild conditions.
New simple route to allylstannanes by zinc-mediated coupling of allyl bromides with Bu3SnCl or Bu2SnCl2 in an H2O (NH4Cl)/THF medium
Carofiglio, Tommaso,Marton, Daniele,Tagliavini, Giuseppe
, p. 2961 - 2963 (2008/10/08)
A new zinc-mediated coupling reaction of allyl and allyl-like bromides with Bu3SnCl (1) or Bu2SnCl2 (2), performed in H2O (NH4Cl)/THF medium, represents an easy route to the following organostannanes: Bu3SnCH2CH=CH2 (3) and Bu2Sn(CH2CH=CH2)2 (4), Bu3Sn(C4H7) (5) and Bu2Sn(C4H7)2 (6) (where C4H7 stands for trans-crotyl, cis-crotyl, or α-methylallyl), and Bu3SnCH=C=CH2 (7). This striking one-pot procedure successfully improves the already general routes where Grignard or other conventional organometallic reagents are used.
