Synthesis, Table of Contents Synthesis 2023; 55(22): 3799-3808DOI: 10.1055/a-2147-1336 paper Palladium/Charcoal-Catalysed Olefin Reduction for the Simple and Efficient Synthesis of Substituted gem-Diborylalkanes Kanak Kanti Das , Debraj Ghorai , Somenath Mahato , Santanu Panda∗ Recommend Article Abstract Buy Article All articles of this category Abstract gem-Diborylalkanes have recently emerged as valuable synthons for diverse C–C bond-forming reactions. They represent an important class of bifunctional reagents that can be applied for the synthesis of simple to complex skeletons. Herein, we report a Pd-catalysed hydrogenation method for the synthesis of gem-diborylalkanes from the corresponding gem-diborylalkenes, which are themselves prepared from the corresponding aldehydes and ketones using known procedures. In addition, transformations of two representative gem-diborylalkane products are discussed leading to a range of functionalised derivatives. Key words Key wordsvinyl geminal B(pin) - alkyl geminal B(pin) - aryl geminal B(pin) - heteroaryl geminal B(pin) - reduction - palladium/carbon Full Text References References 1a Boron-Based Compounds: Potential and Emerging Applications in Medicine. Hawkins-Hey E, Teixidor CV. Wiley-VCH; Weinheim: 2018 1b Synthesis and Application of Organoboron Compounds. In Topics in Organometallic Chemistry, Vol. 49. Fernández E, Whiting A. Springer; Switzerland: 2015 1c Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine. Hall DG. Wiley-VCH; Weinheim: 2005 1d Nandy S, Paul S, Das KK, Kumar P, Ghorai D, Panda S. Org. Biomol. Chem. 2021; 19: 7276 1e Manna S, Das KK, Nandy S, Aich D, Paul S, Panda S. Coord. Chem. Rev. 2021; 448: 214165 1f Hari DP, Abell JC, Fasano V, Aggarwal VK. J. Am. Chem. Soc. 2020; 142: 5515 1g Noble A, Roesner S, Aggarwal VK. Angew. Chem. Int. Ed. 2016; 55: 15920 1h Roesner S, Blair DJ, Aggarwal VK. Chem. Sci. 2015; 6: 3718 1i Zhang C, Hu W, Lovinger GJ, Jin J, Chen J, Morken JP. J. Am. Chem. Soc. 2021; 143: 14189 1j Myhill JA, Wilhelmsen CA, Zhang L, Morken JP. J. Am. Chem. Soc. 2018; 140: 15181 1k Blair DJ, Fletcher CJ, Wheelhouse KM. P, Aggarwal VK. Angew. Chem. Int. Ed. 2014; 53: 5552 1l Liu X, Deaton TM, Haeffner F, Morken JP. Angew. Chem. Int. Ed. 2017; 56: 11485 1m Bold CP, Yeung K, Pape F, Kaiser D, Aggarwal VK. Org. Lett. 2022; 24: 9398 1n Fairchild M, Noble A, Aggarwal VK. Angew. Chem. Int. Ed. 2022; 61: e202205816 1o Fiorito D, Keskin S, Bateman JM, George M, Noble A, Aggarwal VK. J. Am. Chem. Soc. 2022; 144: 7995 1p Cascia EL, Cuenca AB, Fernández E. Chem. Eur. J. 2016; 22: 18737 2a Zhang F, Wu D, Xu Y, Feng XJ. Mater. Chem. 2011; 21: 17590 2b Wagner RW, Lindsey JS. Pure Appl. Chem. 1996; 68: 1373 2c Singh VD, Dwivedi BK, Kumar Y, Pandey DS. New J. Chem. 2021; 45: 1677 3a Hari DP, Madhavachary R, Fasano V, Haire J, Aggarwal VK. J. Am. Chem. Soc. 2021; 143: 7462 3b Wang H, Jing C, Noble A, Aggarwal VK. Angew. Chem. Int. Ed. 2020; 59: 16859 3c Collins BS. L, Wilson CM, Myers EL, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 11700 3d Armstrong RJ, Aggarwal VK. Synthesis 2017; 49: 3323 3e Sandford C, Aggarwal VK. Chem. Commun. 2017; 53: 5481 3f Silvi M, Aggarwal VK. J. Am. Chem. Soc. 2019; 141: 9511 3g Bonet A, Odachowski M, Leonori D, Essafi S, Aggarwal VK. Nat. Chem. 2014; 6: 584 4a Panda S, Ready JM. J. Am. Chem. Soc. 2017; 139: 6038 4b Panda S, Ready JM. J. Am. Chem. Soc. 2018; 140: 13242 4c Das KK, Panda S. Chem. Eur. J. 2020; 26: 14270 4d Das KK, Manna S, Panda S. Chem. Commun. 2021; 57: 441 4e Das KK, Kumar P, Ghorai D, Mondal B, Panda S. Asian J. Org. Chem. 2021; 11: e202100092 4f Manna S, Das KK, Aich D, Panda S. Adv. Synth. Catal. 2021; 363: 2444 5a Paul S, Das KK, Manna S, Panda S. Chem. Eur. J. 2020; 26: 1922 5b Das KK, Panda S. Org. Lett. 2023; 25: 314 5c Das KK, Paul S, Panda S. Org. Biomol. Chem. 2020; 18: 8939 6a Zhang L, Huang Z. J. Am. Chem. Soc. 2015; 137: 15600 6b Uzelac M, Yuan K, Ingleson MJ. Organometallics 2020; 39: 1332 6c Davenport E, Fernández E. Chem. Commun. 2018; 54: 10104 6d Miralles N, Alam R, Szabó KJ, Fernàndez E. Angew. Chem. Int. Ed. 2016; 55: 4303 7a Han S, Lee Y, Jung Y, Cho SH. Angew. Chem. Int. Ed. 2022; 61: e202210532 7b Hwang C, Lee Y, Kim M, Seo Y, Cho SH. Angew. Chem. Int. Ed. 2022; 61: e202209079 7c Kim H, Jung Y, Cho SH. Org. Lett. 2022; 24: 2705 7d Jo W, Lee JH, Cho SH. Chem. Commun. 2021; 57: 4346 7e Lee Y, Han S, Cho SH. Acc. Chem. Res. 2021; 54: 3917 7f Kim M, Park B, Shin M, Kim S, Kim J, Baik M.-H, Cho SH. J. Am. Chem. Soc. 2021; 143: 1069 7g Jo W, Baek S.-y, Hwang C, Heo J, Baik MH, Cho SH. J. Am. Chem. Soc. 2020; 142: 13235 7h Shin M, Kim M, Hwang C, Lee H, Kwon H, Park J, Lee E, Cho SH. Org. Lett. 2020; 22: 2476 7i Kim J, Shin M, Cho SH. ACS Catal. 2019; 9: 8503 7j Lee H, Lee Y, Cho SH. Org. Lett. 2019; 21: 5912 7k Kim J, Cho SH. ACS Catal. 2019; 9: 230 7l Kim J, Hwang C, Kim Y, Cho SH. Org. Process Res. Dev. 2019; 23: 1663 7m Lee Y, Park J, Cho SH. Angew. Chem. Int. Ed. 2018; 57: 12930 7n Kim J, Ko K, Cho SH. Angew. Chem. Int. Ed. 2017; 56: 11584 7o Hwang C, Jo W, Cho SH. Chem. Commun. 2017; 53: 7573 7p Lee Y, Baek S.-y, Park J, Kim S.-T, Tussupbayev S, Kim J, Baik M.-H, Cho SH. J. Am. Chem. Soc. 2017; 139: 976 7q Fernández CE. Chem. Soc. Rev. 2021; 50: 72 7r Salvado O, Fernández E. Chem. Commun. 2021; 57: 6300 7s Gava R, Fernández E. Chem. Eur. J. 2019; 25: 8013 7t Salvado O, Gava R, Fernández E. Org. Lett. 2019; 21: 9247 7u Jo W, Kim J, Choi S, Cho SH. Angew. Chem. Int. Ed. 2016; 55: 9690 7v Park J, Lee Y, Kim J, Cho SH. Org. Lett. 2016; 18: 1210 7w Kim J, Park S, Park J, Cho SH. Angew. Chem. Int. Ed. 2016; 55: 1498 7x Namirembe S, Gao C, Wexler RP, Morken JP. Org. Lett. 2019; 21: 4392 7y Potter B, Szymaniak AA, Edelstein EK, Morken JP. J. Am. Chem. Soc. 2014; 136: 17918 8a Cuenca AB, Fernández E. Chem. Soc. Rev. 2021; 50: 72 8b Babu KN, Massarwe F, Reddy RR, Eghbarieh N, Jakob M, Masarwa A. Molecules 2020; 25: 959 8c Zhang C, Hu W, Morken JP. ACS Catal. 2021; 11: 10660 8d Paul S, Das KK, Aich D, Manna S, Panda S. Org. Chem. Front. 2022; 9: 838 8e Xu N, Liang H, Morken JP. J. Am. Chem. Soc. 2022; 144: 11546 8f Wheatley E, Zanghi JM, Mason MM, Meek SJ. Angew. Chem. Int. Ed. 2023; 62: e202215855 8g Liang MZ, Meek SJ. J. Am. Chem. Soc. 2020; 142: 9925 8h Wheatley E, Zanghi JM, Meek SJ. Org. Lett. 2020; 22: 9269 8i Zanghi JM, Meek SJ. Angew. Chem. Int. Ed. 2020; 59: 8451 8j Green JC, Zanghi JM, Meek SJ. J. Am. Chem. Soc. 2020; 142: 1704 8k Murray SA, Liang MZ, Meek SJ. J. Am. Chem. Soc. 2017; 139: 14061 8l Murray SA, Green JC, Tailor SB, Meek SJ. Angew. Chem. Int. Ed. 2016; 55: 9065 8m Joannou MV, Moyer BS, Goldfogel MJ, Meek SJ. Angew. Chem. Int. Ed. 2015; 54: 14141 8n Murray SA, Luc EC. M, Meek SJ. Org. Lett. 2018; 20: 469 8o Wilhelmsen CA, Zhang X, Myhill JA, Morken JP. Angew. Chem. Int. Ed. 2022; 61: e2021167 8p Sun C, Potter B, Morken JP. J. Am. Chem. Soc. 2014; 136: 6534 8q Law C, Kativhu E, Wang J, Morken JP. Angew. Chem. Int. Ed. 2020; 59: 10311 8r Lovinger GJ, Morken JP. Eur. J. Org. Chem. 2020; 2362 8s Lovinger GJ, Morken JP. J. Am. Chem. Soc. 2017; 139: 17293 8t Lovinger GJ, Aparece MD, Morken JP. J. Am. Chem. Soc. 2017; 139: 3153 8u Zhang L, Lovinger GJ, Edelstein EK, Szymaniak AA, Chierchia MP, Morken JP. Science 2016; 351: 70 8v Cuenca AB, Shishido R, Ito H, Fernández E. Chem. Soc. Rev. 2017; 46: 415 9a Liu X, Sun C, Mlynarski S, Morken JP. Org. Lett. 2018; 20: 1898 9b Namirembe S, Yan L, Morken JP. Org. Lett. 2020; 22: 9174 10 Viereck P, Krautwald S, Pabst TP, Chirik PJ. J. Am. Chem. Soc. 2020; 142: 3923 11 Ito H, Kubotaong K. Org. Lett. 2012; 14: 890 12 Li H, Shangguan X, Zhang Z, Huang S, Zhang Y, Wang J. Org. Lett. 2014; 16: 448 13 Wang L, Zhang T, Sun W, He Z, Xia C, Lan Y, Liu C. J. Am. Chem. Soc. 2017; 139: 5257 14 Liang MZ, Meek SJ. Angew. Chem. Int. Ed. 2019; 58: 14234 15 Endo K, Hirokami M, Shibata T. T. J. Org. Chem. 2010; 75: 3469 16 Iacano CE, Stephens TC, Rajan TS, Pattison GA. J. Am. Chem. Soc. 2018; 140: 2036 17 Li A, Yue G, Li Y, Pan X, Yang T-K. Tetrahedron: Asymmetry 2003; 14: 75 18 Teo JW, Ge S. Angew. Chem. Int. Ed. 2018; 57: 12935 19 Docherty HJ, Nicholson K, Dominey AP, Thomas SP. ACS Catal. 2020; 10: 4686 20 Lin S, Wang L, Aminoleslami N, Lao y, Yagel C, Sharma A. Chem. Sci. 2019; 10: 4684 21 Wang X, Cui X, Li S, Wang Y, Xia C, Jiao H, Wu L. Angew. Chem. Int. Ed. 2020; 59: 13608 22 Nallagonda R, Karimov RR. ACS Catal. 2021; 11: 248 23 Kumar N, Eghbarieh N, Stein T, Shames AI, Masarwa A. Chem. Eur. J. 2020; 26: 5360 24 Wang Q, Biosca M, Himo F, Szabó KJ. Angew. Chem. Int. Ed. 2021; 60: 26327 25 Teo WJ, Ge S. Angew. Chem. Int. Ed. 2018; 57: 1654 26 Kharasch MS, Burt JG. J. Org. Chem. 1951; 16: 150 27 Williams JW. J. Am. Chem. Soc. 1939; 61: 2248 28 Adkins H, Kommes CE, Struss EF, Dasler W. J. Am. Chem. Soc. 1933; 55: 2992 Supplementary Material Supplementary Material Supporting Information
