Synthesis, Table of Contents Synthesis 2021; 53(09): 1654-1662DOI: 10.1055/a-1336-5720 paper Oxidative C–H Acyloxylation of Acetone with Carboxylic Acids under Iodine Catalysis Xiao-Yu Zhou∗ , Xia Chen Recommend Article Abstract Buy Article All articles of this category Abstract Iodine-catalyzed oxidative C(sp3)–H acyloxylation of acetone with carboxylic acids has been developed. The method employs iodide as catalyst and sodium chlorite as oxidant. Substituted benzoic acids, naphthoic acids and heteroaromatic carboxylic acids can be used, and 2-oxopropyl carboxylates are obtained with good to excellent yields. Key words Key wordsiodine - oxidative C–H functionalization - acetone - carboxylic acids - carboxylates Full Text References References and Notes 1a Cavallo G, Metrangolo P, Milani R, Pilati T, Priimagi A, Resnati G, Terraneo G. Chem. Rev. 2016; 116: 2478 1b Heinen F, Engelage E, Dreger A, Weiss R, Huber SM. Angew. Chem. Int. Ed. 2018; 57: 3830 1c Heinen F, Engelage E, Cramer CJ, Huber SM. J. Am. Chem. Soc. 2020; 142: 8633 2a Wirth T. Angew. Chem. Int. Ed. 2005; 44: 3656 2b Dohi T, Ito M, Morimoto K, Iwata M, Kita Y. Angew. Chem. Int. Ed. 2008; 47: 1301 2c Dohi T, Maruyama A, Takenaga N, Senami K, Minamitsuji Y, Fujioka H, Caemmerer SB, Kita Y. Angew. Chem. Int. Ed. 2008; 47: 3787 2d Yoshimura A, Zhdankin VV. Chem. Rev. 2016; 116: 3328 2e Muñiz K. Acc. Chem. Res. 2018; 51: 1507 2f Duhamel T, Stein CJ, Martínez C, Reiher M, Muñiz K. ACS Catal. 2018; 8: 3918 2g Xing B, Ni C, Hu J. Angew. Chem. Int. Ed. 2018; 57: 9896 3 Fischer D, Tomeba H, Pahadi NK, Patil NT, Huo Z, Yamamoto Y. J. Am. Chem. Soc. 2008; 130: 15720 4a Crone B, Kirsch SF, Umland K.-D. Angew. Chem. Int. Ed. 2010; 49: 4661 4b Liu B, Cheng J, Li Y, Li J.-H. Chem. Commun. 2019; 55: 667 5 He Z, Li H, Li Z. J. Org. Chem. 2010; 75: 4636 6 Zhang J, Wu X, Gao Q, Geng X, Zhao P, Wu Y.-D, Wu A. Org. Lett. 2017; 19: 408 7 Gao Q, Yan H, Wu M, Sun J, Yan X, Wu A. Org. Biomol. Chem. 2018; 16: 2342 8 Cai Q, Zhuang S, Yang M, Peng N, Liu Y, Wu A. Tetrahedron 2019; 75: 130756 9 Takeda M, Maejima S, Yamaguchi E, Itoh A. Tetrahedron Lett. 2019; 60: 151284 10 Yin G, Fan L, Ren T, Zheng C, Tao Q, Wu A, She N. Org. Biomol. Chem. 2012; 10: 8877 11 Rao HS. P, Satish V, Kanniyappan S, Kumari P. Tetrahedron 2018; 74: 6047 12 Mani GS, Rao AV. S, Tangella Y, Sunkari S, Sultana F, Namballa HK, Shankaraiah N, Kamal A. New J. Chem. 2018; 42: 15820 13a Marsili LA, Pergomet JL, Gandon V, Riveira MJ. Org. Lett. 2018; 20: 7298 13b Koenig JJ, Arndt T, Gildemeister N, Neudorfl J.-M, Breugst M. J. Org. Chem. 2019; 84: 7587 14 Siddaraju Y, Prabhu KR. ACS Omega 2018; 3: 4908 15 Liu L, Sun Q, Yan Z, Liang X, Zha Z, Yang Y, Wang Z. Green Chem. 2018; 20: 3927 16 Chauhan J, Luthra T, Sen S. Eur. J. Org. Chem. 2018; 4776 17 Tran UP. N, Oss G, Breugst M, Detmar E, Pace DP, Liyanto K, Nguyen TV. ACS Catal. 2019; 9: 912 18a Liu Y, Yuan X, Guo X, Zhang X, Chen B. Tetrahedron 2018; 74: 6057 18b Singh M, Awasthi P, Singh V. Eur. J. Org. Chem. 2020; 1023 19 Zheng Y.-Y, Feng K.-X, Xia A.-B, Liu J, Tang C.-K, Zhou Z.-Y, Xu D.-Q. RSC Adv. 2019; 9: 9770 20 Chen W, Zhu X, Wang F, Yang Y, Deng G, Liang Y. J. Org. Chem. 2020; 85: 3349 21a Yang F.-L, Tian S.-K. Angew. Chem. Int. Ed. 2013; 52: 4929 21b Pandey AK, Chand S, Singh R, Kumar S, Singh KN. ACS Omega 2020; 5: 7627 22 Tanimoto K, Ohkado R, Iida H. J. Org. Chem. 2019; 84: 14980 23 Dey A, Hajra A. J. Org. Chem. 2019; 84: 14904 24 Bhattacharjee P, Bora U. ACS Omega 2019; 4: 11770 25 Sar S, Tripathi A, Dubey KD, Sen S. J. Org. Chem. 2020; 85: 3748 26 Barak DS, Dighe SU, Avasthi I, Batra S. J. Org. Chem. 2018; 83: 3537 27 Siddaraju Y, Prabhu KR. J. Org. Chem. 2018; 83: 11145 28 Sar S, Chauhan J, Sen S. ACS Omega 2020; 5: 4213 29 Ren J, Yan X, Cui X, Pi C, Wu Y, Cui X. Green Chem. 2020; 22: 265 30 Leng J, Meng J, Luo X, Deng W.-P. Tetrahedron 2018; 74: 6993 31a Gao Q, Wu X, Liu S, Wu A. Org. Lett. 2014; 16: 1732 31b Wu X, Gao Q, Liu S, Wu A. Org. Lett. 2014; 16: 2888 31c Liu S, Gao Q, Wu X, Zhang J, Ding K, Wu A. Org. Biomol. Chem. 2015; 13: 2239 31d Zheng K, Zhuang S, Shu W, Wu Y, Yang C, Wu A. Chem. Commun. 2018; 54: 11897 31e Bosnidou AE, Muniz K. Angew. Chem. Int. Ed. 2019; 58: 7485 31f Debnath S, Das T, Gayen S, Ghosh T, Maiti DK. ACS Omega 2019; 4: 20410 32 Liu S, Qi Z, Zhang Z, Qian B. Org. Lett. 2019; 21: 7722 33a Xue Y, Yan Y, Jiang K, Chen W, Yang L. RSC Adv. 2020; 10: 14720 33b Cao Y, Liu L, Huang T, Chen T. New J. Chem. 2020; 44: 8697 34 Tuo X, Chen S, Jiang P, Ni P, Wang X, Deng G.-J. RSC Adv. 2020; 10: 8348 35a Kuwano R. Synthesis 2009; 1049 35b Adly FG. Catalysts 2017; 7: 347 35c Ali MR, Kumar S, Shalmali N, Afzal O, Azim S, Chanana D, Alam O, Paudel YN, Sharma M, Bawa S. Mini-Rev. Med. Chem. 2019; 19: 410 36a Štěpnička P, Demel J, Čejka J. J. Mol. Catal. A: Chem. 2004; 224: 161 36b Kumar CS. C, Kwong HC, Mah SH, Chia TS, Loh W.-S, Quah CK, Lim GK, Chandraju S, Fun H.-K. Molecules 2015; 20: 18827 36c Kulkarni MG, Shaikh YB, Borhade AS, Chavhan SW, Dhondge AP, Gaikwad DD, Desai MP, Birhade DR, Dhatrak NR. Tetrahedron Lett. 2013; 54: 2293 37a Uyanik M, Suzuki D, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2011; 50: 5331 37b Wu Y.-D, Huang B, Zhang Y.-X, Wang X.-X, Dai J.-J, Xu J, Xu H.-J. Org. Biomol. Chem. 2016; 14: 5936 37c Kumar PS, Ravikumar B, Ashalu KC, Reddy KR. Tetrahedron Lett. 2018; 59: 33 37d Wang X, Li G, Yang Y, Jiang J, Feng Z, Zhang P. Chin. Chem. Lett. 2020; 31: 711 38 Ramazani A, Ahmadi Y, Karimi Z, Rezaei A. J. Heterocycl. Chem. 2012; 49: 1447 Supplementary Material Supplementary Material Supporting Information