Synthesis, Table of Contents Synthesis 2021; 53(22): 4231-4238DOI: 10.1055/s-0040-1706046 special topic Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award Synthesis of Borylated Hydrazino Acid Derivatives Chieh-Hung Tien , Alina Trofimova , Wenjie Shao , Andrei K. Yudin∗ Recommend Article Abstract All articles of this category Abstract α-Boryl-α-hydrazinoacetic acid is a highly functionalized boron-containing building block that can be easily accessed from readily available α-borylacetaldehyde. The hydrazine motif can be converted into a variety of α-borylated azoles and diazines in a straightforward protocol. Furthermore, the carboxy group can be derivatized to afford novel organoboron compounds that should find applications in various cross-coupling transformations. Key words Key wordshydrazinoboronates - aminoboronic acids - organoboron - borylated heterocycles - BMIDA Full Text References References 1a Wu X, Chen X.-X, Fossey JS, James TD, Jiang Y.-B. Chem. Soc. Rev. 2013; 42: 8032 1b Dimitrijević E, Taylor MS. ACS Catal. 2013; 3: 945 1c Li J, Ballmer SG, Gillis EP, Fujii S, Schmidt MJ, Palazzolo AM. E, Lehmann JW, Morehouse GF, Burke MD. Science 2015; 347: 1221 1d Smoum R, Rubinstein A, Dembitsky VM, Srebnik M. Chem. Rev. 2012; 112: 4156 2 Diaz DB, Yudin AK. Nat. Chem. 2017; 9: 731 3a Chen D, Frezza M, Schmitt S, Kanwar J, Dou D.-P. Curr. Cancer Drug Targets 2011; 11: 239 3b Adams S, Miller GT, Jesson MI, Watanabe T, Jones B, Wallner BP. Cancer Res. 2004; 64: 5471 3c Seavey MM, Lu LD, Stump KL, Wallace NH, Ruggeri BA. Int. Immunopharmacol. 2012; 12: 257 3d Zhanel GG, Lawrence CK, Adam H, Schweizer F, Zelenitsky S, Zhanel M, Lagacé-Wiens PR. S, Walkty A, Denisuik A, Golden A, Gin AS, Hoban DJ, Lynch JP. III, Karlowsky JA. Drugs 2018; 78: 65 3e Milo LJ. Jr, Lai JH, Wu W, Liu Y, Maw H, Li Y, Jin Z, Shu Y, Poplawski SE, Wu D, Sanford DG, Sudmeier JL, Bachovchin WW. J. Med. Chem. 2011; 54: 4365 4a Andrés P, Ballano G, Calaza I, Cativiela C. Chem. Soc. Rev. 2016; 45: 2291 4b Beenen MA, An C, Ellman JA. J. Am. Chem. Soc. 2008; 130: 6910 4c Zajdlik A, Wang Z, Hickey JL, Aman A, Schimmer AD, Yudin AK. Angew. Chem. Int. Ed. 2013; 52: 8411 4d Diaz DB, Scully CC. G, Liew SK, Adachi S, Trinchera P, St Denis JD, Yudin AK. Angew. Chem. Int. Ed. 2016; 55: 12659 4e Shiro T, Schuhmacher A, Jackl MK, Bode JW. Chem. Sci. 2018; 9: 5191 4f Reyes RL, Sato M, Iwai T, Sawamura M. J. Am. Chem. Soc. 2020; 142: 589 5 Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A. Chem. Rev. 2011; 111: 6984 6a Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. Molecules 2020; 25: 1909 6b Lamberth C. Heterocycles 2007; 71: 1467 6c Da Costa L, Scheers E, Coluccia A, Casulli A, Roche M, Di Giorgio C, Neyts J, Terme T, Cirilli R, La Regina G, Silvestri R, Mirabelli C, Vanelle P. J. Med. Chem. 2018; 61: 8402 7a Salaün A, Potel M, Roisnel T, Gall P, Le Grel P. J. Org. Chem. 2005; 70: 6499 7b Acherar S, Salaün A, Le Grel P, Le Grel B, Jamart-Grégnoire B. Eur. J. Org. Chem. 2013; 2013: 5603 7c Avan I, Hall CD, Katritzky AR. Chem. Soc. Rev. 2014; 43: 3575 7d Suć J, Tumir L.-M, Glavaš-Obrovac L, Jukic M, Piantanida I, Jerić I. Org. Biomol. Chem. 2016; 14: 4865 8a He Z, Yudin AK. J. Am. Chem. Soc. 2011; 133: 13770 8b He Z, Trinchera P, Adachi S, St Denis JD, Yudin AK. Angew. Chem. Int. Ed. 2012; 51: 11092 8c St Denis JD, Zajdlik A, Tan J, Trinchera P, Lee CF, He Z, Adachi S, Yudin AK. J. Am. Chem. Soc. 2014; 136: 17669 8d Kaldas SJ, O’Keefe KT, Mendoza-Sanchez R, Yudin AK. Chem. Eur. J. 2017; 23: 9711 8e Holownia A, Tien C.-H, Diaz DB, Larson RT, Yudin AK. Angew. Chem. Int. Ed. 2019; 58: 15148 9a List B. J. Am. Chem. Soc. 2002; 124: 5656 9b Bøgevig A, Kumaragurubaran N, Juhl K, Zhuang W, Jørgensen KA. Angew. Chem. Int. Ed. 2002; 41: 1790 10 Based on separation by HPLC on a chiral stationary phase column (see Supporting Information), the e.r. of 6d, and thus 1 by correlation, was determined to be 60:40. Due to the almost racemic nature of 1, e.r. determination of derivatives 5 and 6 were not measured. 11 Ivon YM, Mazurenko IV, Kuchkovska YO, Voitenko ZV, Grygorenko OO. Angew. Chem. Int. Ed. 2020; 59: 18016 12 Bindal S, Kumar D, Kommi DN, Bhatiya S, Chakraborti AK. Synthesis 2011; 1930 13 Hou T.-C, Wu Y.-Y, Chiang P.-Y, Tan K.-T. Chem. Sci. 2015; 6: 4643 Supplementary Material Supplementary Material Supporting Information
