Synthesis, Table of Contents Synthesis 2018; 50(09): 1857-1861DOI: 10.1055/s-0036-1591926 paper © Georg Thieme Verlag Stuttgart · New York 1-(Trimethylsilyl)vinyl MIDA Boronate: A Trifunctional C2 Building Block Yevhen M. Ivon a Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine b National Taras Shevchenko University of Kyiv, Volodymyrska Street, 60, Kyiv 01601, Ukraine Email: gregor@univ.kiev.ua , Zoya V. Voitenko b National Taras Shevchenko University of Kyiv, Volodymyrska Street, 60, Kyiv 01601, Ukraine Email: gregor@univ.kiev.ua , Oleksandr O. Grygorenko * a Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine b National Taras Shevchenko University of Kyiv, Volodymyrska Street, 60, Kyiv 01601, Ukraine Email: gregor@univ.kiev.ua › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract 1-(Trimethylsilyl)vinyl MIDA boronate — a trifunctional C2 building block — is prepared in only two laboratory steps and 54% overall yield starting from readily available trimethyl(vinyl)silane. The title compound undergoes orthogonal functionalization at either of the groups present in its structure, for example, iodination at the trimethylsilyl moiety, epoxidation at the double bond, and Suzuki–Miyaura coupling at the MIDA boronate. Key words Key wordsorganosilicon compounds - organoboron compounds - alkenes - Suzuki–Miyaura coupling - orthogonal reactions Full Text References References 1 Hall DG. In Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials. Hall DG. Wiley-VCH; Weinheim: 2011: 1-133 2 Woerly EM. Roy J. Burke MD. Nature 2014; 6: 484 3 Lee SJ. Anderson TM. Burke MD. Angew. Chem. Int. Ed. 2010; 49: 8860 4 He Z. Zajdlik A. Yudin AK. Acc. Chem. Res. 2014; 47: 1029 5 He G. Chen S. Wang Q. Huang H. Zhang Q. Zhang D. Zhang R. Zhu H. Org. Biomol. Chem. 2014; 12: 5945 6 He G. Zhang Q. Huang H. Chen S. Wang Q. Zhang D. Zhang R. Zhu H. Eur. J. Org. Chem. 2013; 6979 7 Saito N. Saito K. Sato H. Sato Y. Adv. Synth. Catal. 2013; 355: 853 8 St Denis JD. Zajdlik A. Tan J. Trinchera P. Lee CF. He Z. Adachi S. Yudin AK. J. Am. Chem. Soc. 2014; 136: 17669 9 He Z. Trinchera P. Adachi S. St Denis JD. Yudin AK. Angew. Chem. Int. Ed. 2012; 51: 11092 10 Katz JD. Lapointe BT. Dinsmore CJ. J. Org. Chem. 2009; 74: 8866 11 Percy JM. Emerson H. Fyfe JW. B. Kennedy AR. Maciuk S. Orr D. Rathouská L. Redmond JM. Wilson PG. Chem. Eur. J. 2016; 22: 12166 12 Tatsuya W. Yuto S. Azusa K. Hideki Y. Koichiro O. Bull. Chem. Soc. Jpn. 2009; 82: 1433 13 Xu S. Lee C.-T. Rao H. Negishi E. Adv. Synth. Catal. 2011; 353: 2981 14 Woerly EM. Miller JE. Burke MD. Tetrahedron 2013; 69: 7732 15 Jiao J. Hyodo K. Hu H. Nakajima K. Nishihara Y. J. Org. Chem. 2014; 79: 285 16 Chae YM. Bae JS. Moon JH. Lee JY. Yun J. Adv. Synth. Catal. 2014; 356: 843 17 La Cascia E. Cuenca AB. Fernández E. Chem. Eur. J. 2016; 22: 18737 18 Bhat NG. Aguirre CP. Tetrahedron Lett. 2000; 41: 8027 19 Kurahashi T. Hata T. Masai H. Kitagawa H. Shimizu M. Hiyama T. Tetrahedron 2002; 58: 6381 20 Hata T. Kitagawa H. Masai H. Kurahashi T. Shimizu M. Hiyama T. Angew. Chem. Int. Ed. 2001; 40: 790 21 Mora-Radó H. Bialy L. Czechtizky W. Méndez M. Harrity JP. A. Angew. Chem. Int. Ed. 2016; 55: 5834 22 Ferrand L. Lyu Y. Rivera-Hernández A. Fallon BJ. Amatore M. Aubert C. Petit M. Synthesis 2017; 49: 3895 23 Hyodo K. Suetsugu M. Nishihara Y. Org. Lett. 2014; 16: 440 24 Darses S. Genet J.-P. Chem. Rev. 2008; 108: 288 25 Molander GA. Ellis N. Acc. Chem. Res. 2007; 40: 275 26 Gillis EP. Burke MD. Aldrichimica Acta 2009; 42: 17 27 Kublicki M. Dąbrowski M. Durka K. Kliś T. Serwatowski J. Woźniak K. Tetrahedron Lett. 2017; 58: 2162 28 Kalinin AV. Scherer S. Snieckus V. Angew. Chem. Int. Ed. 2003; 42: 3399 29 Boeckman RK. Jr. Blum DM. Ganem B. Halvey N. Org. Synth. 1978; 58: 152 30 Edelstein EK. Namirembe S. Morken JP. J. Am. Chem. Soc. 2017; 139: 5027 31 Dick GR. Knapp DM. Gillis EP. Burke MD. Org. Lett. 2010; 12: 2314 32 Struble JR. Lee SJ. Burke MD. Tetrahedron 2010; 66: 4710 33 Armarego WL. F. Chai C. Purification of Laboratory Chemicals. 5th ed. Elsevier; Oxford: 2003 34 Oliva A. Molinari A. Synth. Commun. 1985; 15: 707 Supplementary Material Supplementary Material Supporting Information
