Synthesis, Table of Contents Synthesis 2024; 56(04): 573-576DOI: 10.1055/a-2169-6200 special topic Synthetic Development of Key Intermediates and Active Pharmaceutical Ingredients (APIs) Bis(pinacoloto)diboron/4-Phenylpyridine System for One-Pot Photocatalyzed Borylation and Reduction of Aldehyde: Synthesis of Tavaborole in a Flow Reactor Authors Kankanala Naveen Kumar‡ Mouzma Mhate‡ Velayutham Ravichandiran Sharada Prasanna Swain ∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract A photocatalyzed one-pot borylation of haloarene and reduction of aldehyde by cocatalysis of bis(pinacoloto)diboron/4-phenylpyridine is reported. The reaction was carried out in a flow reactor by irradiating the reaction at 410 nm, with residence time of 10 minutes. The method was successfully applied for the synthesis of tavaborole in a single step with 81% yield. Key words Key wordstavaborole - photocatalysis - flow chemistry - green chemistry - one-pot synthesis Full Text References References 1 Baker SJ, Ding CZ, Akama T, Zhang Y, Hernandez V, Xia Y. Future Med. Chem. 2009; 1: 1275 2a Messner K, Vuong B, Tranmer GK. Pharmaceuticals 2022; 15: 264 2b Mahanta CS, Ravichandiran V, Swain SP. ACS Appl. Bio Mater. 2023; 6: 2995 3 Leśnikowski ZJ. J. Med. Chem. 2016; 59: 7738 4 Elewski BE, Aly R, Baldwin SL, González Soto RF, Rich P, Weisfeld M, Wiltz H, Zane LT, Pollak R. J. Am. Acad. Dermatol. 2015; 73: 62 5 Ishiyama T, Murata M, Miyaura N. J. Org. Chem. 1995; 60: 7508 6 Chen K, Zhang S, Hea P, Li P. Chem. Sci. 2016; 7: 3676 7 Mfuh AM, Doyle JD, Chhetri B, Arman HD, Larionov OV. J. Am. Chem. Soc. 2016; 138: 2985 8 Zhang L, Jiao L. J. Am. Chem. Soc. 2019; 141: 9124 9 Zhang L, Wu Z.-Q, Jiao L. Angew. Chem. Int. Ed. 2020; 59: 2095 10 Wang G, Zhang H, Zhao J, Li W, Cao J, Zhu C, Li S. Angew. Chem. Int. Ed. 2016; 55: 5985 11a Baker SJ, Akama T, Alley MR. K, Benkovic SJ, DiPierro M, Hernandez VS, Hold KM, Kennedy I, Likhotvorik I, Mao W, Maples KR, Plattner JJ, Rock F, Sanders V, Stemphoski AM, Petros G, Siead Y, Yong-Kang Z, Zhou ZH. US Patent 8115026B2, 2012 11b Pullagurla MR, Valsan M, Kumar N, Pitta BR, Rangisetty JB. US Patent 10435419B2, 2019 12 Subramanian S, Rajender K, Joma M, Samir C, Shekhar N, Bhirud B. US10457695B2, 2019 13a Erythropela HC, Zimmermana JB, de Wintera TM, Petitjeana L, Melnikova F, Lama CH, Lounsburya AW, Mellora KE, Jankovíca NZ, Tu Q, Pincusa LN, Falinskia MM, Shia W, Coish P, Plata DL, Anastasa PT. Green Chem. 2018; 20: 1929 13b Swain SP, Shri O, Ravichandiran V. Mol. Catal. 2012; 508: 111576 13c Maury SK, Singh S. Synthesis 2023; 55: 755 13d Swain SP, Kumar KN, Mhate M, Panchami H, Ravichandiran V. Mol. Catal. 2022; 522: 112210 13e Kumar KN, Reddy MM, Panchami H, Ravichandiran V, Dhaked DK, Swain SP. Mol. Catal. 2022; 524: 112324 14 Benjamin DA, Hook WD, Paul R, Hirst MP, Malcolm BB, Booker-Milburn KI. J. Org. Chem. 2005; 70: 7558 15a Porta R, Benaglia M, Puglisi A. Org. Process Res. Dev. 2016; 20: 2 15b Zhelavskyi O, Jhang Y.-J, Nagorny P. Synthesis 2023; 55: 2361 16a Mhate M, Gautam A, Kumar KN, Ravichandiran V, Swain SP. Mol. Catal. 2023; 546: 113246 16b Mhate M, Mahanta CS, Dhaked DK, Ravichandiran V, Swain SP. Chem. Commun. 2023; 59: 10920 17 Wang G, Cao J, Gao L, Chen W, Huang W, Cheng X, Li S. J. Am. Chem. Soc. 2017; 139: 3904 18 Swain SP, Ravichandiran V, Mhate M, Kumar KN. Indian Patent 202331058995, 2023 19 Swain SP, Ravichandiran V, Mhate M, Kumar KN. Indian Patent 202331058996, 2023 Supplementary Material Supplementary Material Supporting Information (PDF)
