Synlett, Inhaltsverzeichnis Synlett 2018; 29(11): 1415-1420DOI: 10.1055/s-0036-1591958 synpacts © Georg Thieme Verlag Stuttgart · New YorkSynthetic Transformations of Alkenyl MIDA Boronates toward the Efficient Construction of Organoborons Autor*innen Institutsangaben Honggen Wang* a School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China eMail: wanghg3@mail.sysu.edu.cn Yao-Fu Zeng b Institute of Pharmacy & Pharmacology, University of South China, Hengyang 421001, P. R. of China Wen-Xin Lv a School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China eMail: wanghg3@mail.sysu.edu.cn Dong-Hang Tan a School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China eMail: wanghg3@mail.sysu.edu.cn Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Dedicated to Professor Lian-Quan Gu. Abstract The attachment of N-methyliminodiacetyl boron (MIDA boron) to alkenes leads to a new type of activated alkenes. Synthetic manipulation of the alkene double bond while retaining the boron moiety offers an unprecedented opportunity for the construction of organoborons. These reactions feature unique reactivity, good regioselectivity, and they can be used to access organoborons that are historically difficult to prepare. Herein, we give a brief summary of advances in the use of alkenyl MIDA boronates as starting materials for organoboron synthesis. Mechanisms are discussed where relevant. Key words Key wordsalkenes - boranes - organoboron compounds - oxidation - sp3 hybridization Volltext Referenzen References 1a Contemporary Boron Chemistry . Davidson MG. Hughes AK. Marder TB. Wade K. Royal Society of Chemistry; Cambridge: 2000 1b Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials. Hall DG. Wiley-VCH; Weinheim: 2011. 2nd ed. 1c Jana R. Pathak TP. Sigman MS. Chem. Rev. 2011; 111: 1417 2 Carrow BP. Hartwig JF. J. Am. Chem. Soc. 2011; 133: 2116 3 Brown H. Rao BC. J. Org. Chem. 1957; 22: 1137 4 Petasis NA. Akritopoulou I. Tetrahedron Lett. 1993; 34: 583 5 Thomas SP. French RM. Jheengut V. Aggarwal VK. Chem. Rec. 2009; 9: 24 6a Darses S. Genet J.-P. Chem. Rev. 2008; 108: 288 6b Noguchi H. Hojo K. Suginome M. J. Am. Chem. Soc. 2007; 129: 758 7a Gillis EP. Burke MD. J. Am. Chem. Soc. 2007; 129: 6716 7b Li J. Ballmer SG. Gillis EP. Fujii S. Schmidt MS. Palazzolo AM. E. Lehmann JW. Morehouse GF. Burke MD. Science 2015; 347: 1221 8a Lennox AJ. J. Lloyd-Jones GC. Chem. Soc. Rev. 2014; 43: 412 8b Berionni G. Maji B. Knochel P. Mayr H. Chem. Sci. 2012; 3: 878 9 Knapp DM. Gillis EP. Burke MD. J. Am. Chem. Soc. 2009; 131: 6961 10a Quiclet-Sire B. Zard SZ. J. Am. Chem. Soc. 2015; 137: 6762 10b Heinrich MR. Sharp LA. Zard SZ. Chem. Commun. 2005; 3077 11a Ibrahim MR. Bühl M. Knab R. Von Rague Schleyer P. J. Comput. Chem. 1992; 13: 423 11b Dang L. Lin Z. Organometallics 2008; 27: 4443 For selected examples, see: 12a Kobayashi M. Sanda F. Endo T. Macromolecules 2002; 35: 346 12b Ansorge A. Brauer DJ. Bürger H. Hagen T. Pawelke G. J. Organomet. Chem. 1993; 444: 5 12c Li X. Curran DP. J. Am. Chem. Soc. 2013; 135: 12076 12d Cheng Q.-Q. Zhu S.-F. Zhang Y.-Z. Xie X.-L. Zhou Q.-L. J. Am. Chem. Soc. 2013; 135: 14094 12e Chen D. Zhang X. Qi W.-Y. Xu B. Xu M.-H. J. Am. Chem. Soc. 2015; 137: 5268 13 He Z. Yudin AK. J. Am. Chem. Soc. 2011; 133: 13770 14 Li J. Burke MD. J. Am. Chem. Soc. 2011; 133: 13774 15 Lv W.-X. Zeng Y.-F. Li Q. Chen Y. Tan D.-H. Yang L. Wang H. Angew. Chem. Int. Ed. 2016; 55: 10069 16a Scharnagl FK. Bose SK. Marder TB. Org. Biomol. Chem. 2017; 15: 1738 16b Noda H. Bode JW. Org. Biomol. Chem. 2016; 14: 16 16c St Denis JD. He Z. Yudin AK. ACS Catal. 2015; 5: 5373 17 Dumas AM. Molander GA. Bode JW. Angew. Chem. Int. Ed. 2012; 51: 5683 18 Taguchi J. Ikeda T. Takahashi R. Sasaki I. Ogasawara Y. Dairi T. Kato N. Yamamoto Y. Bode JW. Ito H. Angew. Chem. Int. Ed. 2017; 56: 13847 19 Lepage ML. Lai S. Peressin N. Hadjerci R. Patrick BO. Perrin DM. Angew. Chem. Int. Ed. 2017; 56: 15257 20 Lee CF. Holownia A. Bennett JM. Elkins JM. St Denis JD. Adachi S. Yudin AK. Angew. Chem. Int. Ed. 2017; 56: 6264 21 Khanizeman RN. Barde E. Bates RW. Guérinot A. Cossy J. Org. Lett. 2017; 19: 5046 22a Lhermet R. Ahmad M. Fressigné C. Silvi B. Durandetti M. Maddaluno J. Chem. Eur. J. 2014; 20: 10249 22b Satoh M. Miyaura N. Suzuki A. Chem. Lett. 1986; 1329 22c Xu S. Lee C.-T. Rao H. Negishi E.-i. Adv. Synth. Catal. 2011; 353: 2981 22d Cascia EL. Cuenca AB. Fernández E. Chem. Eur. J. 2016; 22: 18737 23 Zeng Y.-F. Ji W.-W. Lv W.-X. Chen Y. Tan D.-H. Li Q. Wang H. Angew. Chem. Int. Ed. 2017; 56: 14707
