Synthesis, Table of Contents Synthesis 2021; 53(08): 1513-1523DOI: 10.1055/s-0040-1705972 paper Nickel(II)- and Silver(I)-Catalyzed C–H Bond Halogenation of Anilides and Carbamates Ebrahim Kianmehr∗ , Hadi Afaridoun Recommend Article Abstract Buy Article All articles of this category Abstract ortho-C–H bond halogenation of anilides and N-aryl carbamates using easily available N-halosuccinimides (NXS) as the active halogenation reagent in the presence of nickel or silver catalyst has been developed. This method provides a new approach to 2-haloanilides and carbamates, which may serve as starting materials for the synthesis of pharmaceutically and biologically active compounds. Key words Key wordscross-coupling reactions - C–H activation - homogeneous catalysis - halogenation - nickel - silver Full Text References References 1a Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174 1b Kakiuchi F, Kochi T. Synthesis 2008; 3013 1c Li B.-J, Yang S.-D, Shi Z.-J. Synlett 2008; 949 1d Li C.-J. Acc. Chem. Res. 2008; 42: 335 1e Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792 1f Chen X, Engle KM, Wang DH, Yu JQ. Angew. Chem. Int. Ed. 2009; 48: 5094 1g Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2009; 110: 624 1h Kakiuchi F, Kochi T, Mutsutani H, Kobayashi N, Urano S, Sato M, Nishiyama S, Tanabe T. J. Am. Chem. Soc. 2009; 131: 11310 1i Yang L, Lu Z, Stahl SS. Chem. Commun. 2009; 6460 1j Zhao X, Dimitrijevic E, Dong VM. J. Am. Chem. Soc. 2009; 131: 3466 1k Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147 1l Mo F, Yan JM, Qiu D, Li F, Zhang Y, Wang J. Angew. Chem. 2010; 122: 2072 1m Satoh T, Miura M. Chem. Eur. J. 2010; 16: 11212 1n Song B, Zheng X, Mo J, Xu B. Adv. Synth. Catal. 2010; 352: 329 1o Sun C.-L, Li B.-J, Shi Z.-J. Chem. Commun. 2010; 46: 677 1p Tang ML, Bao Z. Chem. Mater. 2010; 23: 446 1q Xu L.-M, Li B.-J, Yang Z, Shi Z.-J. Chem. Soc. Rev. 2010; 39: 712 1r Dubost E, Fossey C, Cailly T, Rault S, Fabis F. J. Org. Chem. 2011; 76: 6414 2a Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2011; 45: 788 2b Wencel-Delord J, Droege T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740 2c Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215 2d Colby DA, Tsai AS, Bergman RG, Ellman JA. Acc. Chem. Res. 2012; 45: 814 2e Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062 2f Yao B, Wang Z.-L, Zhang H, Wang D.-X, Zhao L, Wang M.-X. J. Org. Chem. 2012; 77: 3336 2g Collins KD, Glorius F. Tetrahedron 2013; 69: 7817 2h Kuhl N, Schröder N, Glorius F. Org. Lett. 2013; 15: 3860 2i Sun C.-L, Shi Z.-J. Chem. Rev. 2014; 114: 9219 2j Yu D.-G, Gensch T, de Azambuja F, Vásquez-Céspedes S, Glorius F. J. Am. Chem. Soc. 2014; 136: 17722 2k Weix DJ. Acc. Chem. Res. 2015; 48: 1767 2l Lied F, Lerchen A, Knecht T, Mück-Lichtenfeld C, Glorius F. ACS Catal. 2016; 6: 7839 2m Ruiz-Castillo P, Buchwald SL. Chem. Rev. 2016; 116: 12564 2n Tellis JC, Kelly CB, Primer DN, Jouffroy M, Patel NR, Molander GA. Acc. Chem. Res. 2016; 49: 1429 2o Tang R.-J, Milcent T, Crousse B. J. Org. Chem. 2018; 83: 930 3a Littke AF, Fu GC. Angew. Chem. Int. Ed. 1998; 37: 3387 3b Stürmer R. Angew. Chem. Int. Ed. 1999; 38: 3307 3c Evans DA, Katz JL, Peterson GS, Hintermann T. J. Am. Chem. Soc. 2001; 123: 12411 3d Tan KL, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2001; 123: 2685 3e Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176 3f Spielvogel DJ, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 3500 3g Lail M, Arrowood BN, Gunnoe TB. J. Am. Chem. Soc. 2003; 125: 7506 3h Tsukada N, Mitsuboshi T, Setoguchi H, Inoue Y. J. Am. Chem. Soc. 2003; 125: 12102 3i Shi Z, He C. J. Am. Chem. Soc. 2004; 126: 13596 3j Choudary BM, Sridhar C, Kantam ML, Venkanna GT, Sreedhar B. J. Am. Chem. Soc. 2005; 127: 9948 3k Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442 4a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457 4b Brennführer A, Neumann H, Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114 4c Vo GD, Hartwig JF. J. Am. Chem. Soc. 2009; 131: 11049 4d Wang X, Mei T.-S, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 7520 4e Chen J, Xiong X, Chen Z, Huang J. Synlett 2015; 26: 2831 5a Hodgson HH. Chem. Rev. 1947; 40: 251 5b Dubey SK, Singh AK, Singh H, Sharma S, Iyer RN, Katiyar JC, Goel P, Sen AB. J. Med. Chem. 1978; 21: 1178 5c Snieckus V. Chem. Rev. 1990; 90: 879 5d Podgoršek A, Zupan M, Iskra J. Angew. Chem. Int. Ed. 2009; 48: 8424 5e Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451 5f Janin YL. Chem. Rev. 2012; 112: 3924 5g Kolvari E, Amoozadeh A, Koukabi N, Otokesh S, Isari M. Tetrahedron Lett. 2014; 55: 3648 5h Saikia I, Borah AJ, Phukan P. Chem. Rev. 2016; 116: 6837 5i Xiong X, Yeung YY. Angew. Chem. Int. Ed. 2016; 55: 16101 5j Mostafa MA. B, Bowley RM, Racys DT, Henry MC, Sutherland A. J. Org. Chem. 2017; 82: 7529 6a Narender N, Srinivasu P, Ramakrishna Prasad M, Kulkarni SJ, Raghavan KV. Synth. Commun. 2002; 32: 2313 6b Krishna Mohan KV. V, Narender N, Srinivasu P, Kulkarni SJ, Raghavan KV. Synth. Commun. 2004; 34: 2143 6c Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074 6d Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242 6e Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624 6f Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147 6g Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740 6h Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879 6i Ackermann L. Acc. Chem. Res. 2014; 47: 281 6j Zhang M, Zhang Y, Jie X, Zhao H, Li G, Su W. Org. Chem. Front. 2014; 1: 843 6k Chen Z, Wang B, Zhang J, Yu W, Liu Z, Zhang Y. Org. Chem. Front. 2015; 2: 1107 6l Liao G, Shi B. Acta Chim. Sinica 2015; 73: 1283 6m Zhan B.-B, Liu Y.-H, Hu F, Shi B.-F. Chem. Commun. 2016; 52: 4934 6n Bovonsombat P, Teecomegaet P, Kulvaranon P, Pandey A, Chobtumskul K, Tungsirisurp S, Sophanpanichkul P, Losuwanakul S, Soimaneewan D, Kanjanwongpaisan P. Tetrahedron 2017; 73: 6564 7a Mei T.-S, Giri R, Maugel N, Yu J.-Q. Angew. Chem. Int. Ed. 2008; 47: 5215 7b Kakiuchi F, Kochi T, Mutsutani H, Kobayashi N, Urano S, Sato M, Nishiyama S, Tanabe T. J. Am. Chem. Soc. 2009; 131: 11310 7c Sheppard TD. Org. Biomol. Chem. 2009; 7: 1043 7d Zhao X, Dimitrijević E, Dong VM. J. Am. Chem. Soc. 2009; 131: 3466 7e Shen X, Hyde AM, Buchwald SL. J. Am. Chem. Soc. 2010; 132: 14076 7f Song B, Zheng X, Mo J, Xu B. Adv. Synth. Catal. 2010; 352: 329 7g Wang W, Pan C, Chen F, Cheng J. Chem. Commun. 2011; 47: 3978 7h Schröder N, Wencel-Delord J, Glorius F. J. Am. Chem. Soc. 2012; 134: 8298 7i Kuhl N, Schröder N, Glorius F. Org. Lett. 2013; 15: 3860 7j Mo S, Zhu Y, Shen Z. Org. Biomol. Chem. 2013; 11: 2756 8a Suess AM, Ertem MZ, Cramer CJ, Stahl SS. J. Am. Chem. Soc. 2013; 135: 9797 8b Sun X, Shan G, Sun Y, Rao Y. Angew. Chem. Int. Ed. 2013; 52: 4440 8c Truong T, Klimovica K, Daugulis O. J. Am. Chem. Soc. 2013; 135: 9342 8d Wang X.-C, Hu Y, Bonacorsi S, Hong Y, Burrell R, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 10326 8e Chu L, Xiao K.-J, Yu J.-Q. Science 2014; 346: 451 8f Du Z.-J, Gao L.-X, Lin Y.-J, Han F.-S. ChemCatChem 2014; 6: 123 8g Gao D.-W, Gu Q, You S.-L. ACS Catal. 2014; 4: 2741 8h Hwang H, Kim J, Jeong J, Chang S. J. Am. Chem. Soc. 2014; 136: 10770 8i Qian G, Hong X, Liu B, Mao H, Xu B. Org. Lett. 2014; 16: 5294 8j Wang L, Ackermann L. Chem. Commun. 2014; 50: 1083 8k Yu D.-G, Gensch T, de Azambuja F, Vásquez-Céspedes S, Glorius F. J. Am. Chem. Soc. 2014; 136: 17722 8l Zhang Q, Yang F, Wu Y. Org. Chem. Front. 2014; 1: 694 8m Li B, Liu B, Shi B.-F. Chem. Commun. 2015; 51: 5093 8n Schröder N, Lied F, Glorius F. J. Am. Chem. Soc. 2015; 137: 1448 8o Lied F, Lerchen A, Knecht T, Mück-Lichtenfeld C, Glorius F. ACS Catal. 2016; 6: 7839 8p Maddox SM, Dinh AN, Armenta F, Um J, Gustafson JL. Org. Lett. 2016; 18: 5476 8q Moghaddam FM, Tavakoli G, Saeednia B, Langer P, Jafari B. J. Org. Chem. 2016; 81: 3868 8r Petrone DA, Ye J, Lautens M. Chem. Rev. 2016; 116: 8003 8s Zhan B.-B, Liu Y.-H, Hu F, Shi B.-F. Chem. Commun. 2016; 52: 4934 8t Liu X.-H, Park H, Hu J.-H, Hu Y, Zhang Q.-L, Wang B.-L, Sun B, Yeung K.-S, Zhang F.-L, Yu J.-Q. J. Am. Chem. Soc. 2017; 139: 888 8u Li Z.-L, Wu P.-Y, Cai C. New J. Chem. 2019; 43: 3462 9a Guette C, Essayegh M, Desbene PL, Basselier JJ. Synth. Commun. 1986; 16: 1641 9b Olah GA, Ohannesian L, Arvanaghi M. Synthesis 1986; 868 9c Smith K, James DM, Matthews I, Bye MR. J. Chem. Soc., Perkin Trans. 1 1992; 1877 9d Rao R. Synth. Commun. 1993; 23: 779 9e Mashraqui SH, Mudaliar CD, Hariharasubrahmanian H. Tetrahedron Lett. 1997; 38: 4865 9f Srinivasu P, Ramakrishna Prasad M, Kulkarni SJ, Raghavan KV. Synth. Commun. 2002; 32: 2313 9g Narender N, Krishna Mohan KV. V, Reddy RV, Srinivasu P, Kulkarni SJ, Raghavan KV. J. Mol. Catal. A: Chem. 2003; 192: 73 9h Singhal S, Jain SL, Sain B. J. Mol. Catal. A: Chem. 2006; 258: 198 9i Adibi H, Hajipour AR, Hashemi M. Tetrahedron Lett. 2007; 48: 1255 9j Roy S, Saha M, Bhar S. Synth. Commun. 2007; 37: 579 9k Stropnik T, Bombek S, Kočevar M, Polanc S. Tetrahedron Lett. 2008; 49: 1729 9l Borikar SP, Daniel T, Paul V. Tetrahedron Lett. 2009; 50: 1007 9m Zhou C.-Y, Li J, Peddibhotla S, Romo D. Org. Lett. 2010; 12: 2104 9n Jakab G, Hosseini A, Hausmann H, Schreiner PR. Synthesis 2013; 45: 1635 9o Maibunkaew T, Thongsornkleeb C, Tummatorn J, Bunrit A, Ruchirawat S. Synlett 2014; 25: 1769 9p Bovonsombat P, Sophanpanichkul P, Pandey A, Tungsirisurp S, Limthavornlit P, Chobtumskul K, Kuhataparuk P, Sathityatiwat S, Teecomegaet P. Tetrahedron Lett. 2015; 56: 2193 10a Bovonsombat P, McNelis E. Synthesis 1993; 237 10b Goldberg Y, Alper H. J. Org. Chem. 1993; 58: 3072 10c Paul V, Sudalai A, Daniel T, Srinivasan KV. Tetrahedron Lett. 1994; 35: 7055 10d Oberhauser T. J. Org. Chem. 1997; 62: 4504 10e Castanet A.-S, Colobert F, Broutin P.-E. Tetrahedron Lett. 2002; 43: 5047 10f Tanemura K, Suzuki T, Nishida Y, Satsumabayashi K, Horaguchi T. Chem. Lett. 2003; 32: 932 10g Prakash GK. S, Mathew T, Hoole D, Esteves PM, Wang Q, Rasul G, Olah GA. J. Am. Chem. Soc. 2004; 126: 15770 10h Ganguly NC, De P, Dutta S. Synthesis 2005; 1103 10i Zhang Y, Shibatomi K, Yamamoto H. Synlett 2005; 2837 10j Das B, Venkateswarlu K, Majhi A, Siddaiah V, Reddy KR. J. Mol. Catal. A: Chem. 2007; 267: 30 10k Bovonsombat P, Ali R, Khan C, Leykajarakul J, Pla-on K, Aphimanchindakul S, Pungcharoenpong N, Timsuea N, Arunrat A, Punpongjareorn N. Tetrahedron 2010; 66: 6928 10l Mo F, Yan JM, Qiu D, Li F, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2010; 49: 2028 10m Qiu D, Mo F, Zheng Z, Zhang Y, Wang J. Org. Lett. 2010; 12: 5474 10n Racys DT, Sharif SA. I, Pimlott SL, Sutherland A. J. Org. Chem. 2016; 81: 772 11a Wan X, Ma Z, Li B, Zhang K, Cao S, Zhang S, Shi Z. J. Am. Chem. Soc. 2006; 128: 7416 11b Bedford RB, Engelhart JU, Haddow MF, Mitchell CJ, Webster RL. Dalton Trans. 2010; 10464 11c Bedford RB, Haddow MF, Mitchell CJ, Webster RL. Angew. Chem. 2011; 123: 5638 11d Schröder N, Wencel-Delord J, Glorius F. J. Am. Chem. Soc. 2012; 134: 8298 11e Urones B, Martínez ÁM, Rodriguez N, Arrayás RG, Carretero JC. Chem. Commun. 2013; 49: 11044 11f Hering T, König B. Tetrahedron 2016; 72: 7821 11g Racys DT, Sharif SA. I, Pimlott SL, Sutherland A. J. Org. Chem. 2016; 81: 772 11h Das R, Kapur M. J. Org. Chem. 2017; 82: 1114 11i Kathiravan S, Nicholls IA. Chem. Eur. J. 2017; 23: 7031 11j Zhang L, Hu X. Chem. Sci. 2017; 8: 7009 11k Dubost E, Babin V, Benoist F, Hébert A, Barbey P, Chollet C. l, Bouillon J.-P, Manrique A, Pieters G, Fabis F, Cailly T. Org. Lett. 2018; 20: 6302 11l Li Z.-l, Sun K.-k, Cai C. Org. Biomol. Chem. 2018; 16: 5433 12a Lou S, Fu GC. J. Am. Chem. Soc. 2010; 132: 5010 12b Hu X. Chem. Sci. 2011; 2: 1867 12c Jensen KL, Standley EA, Jamison TF. J. Am. Chem. Soc. 2014; 136: 11145 12d Xiao YL, Guo WH, He GZ, Pan Q, Zhang X. Angew. Chem. Int. Ed. 2014; 53: 9909 12e An L, Xiao YL, Min QQ, Zhang X. Angew. Chem. Int. Ed. 2015; 54: 9079 12f Arendt KM, Doyle AG. Angew. Chem. Int. Ed. 2015; 54: 9876 12g Gutierrez O, Tellis JC, Primer DN, Molander GA, Kozlowski MC. J. Am. Chem. Soc. 2015; 137: 4896 12h Magano J, Monfette S. ACS Catal. 2015; 5: 3120 12i Tollefson EJ, Hanna LE, Jarvo ER. Acc. Chem. Res. 2015; 48: 2344 12j Whittaker AM, Dong VM. Angew. Chem. Int. Ed. 2015; 54: 1312 12k Oderinde MS, Frenette M, Robbins DW, Aquila B, Johannes JW. J. Am. Chem. Soc. 2016; 138: 1760 12l Wang J, Qin T, Chen TG, Wimmer L, Edwards JT, Cornella J, Vokits B, Shaw SA, Baran PS. Angew. Chem. Int. Ed. 2016; 55: 9676 12m Shih B.-H, Basha RS, Lee CF. ACS Catal. 2019; 9: 8862 12n Huang L, Ji T, Rueping M. J. Am. Chem. Soc. 2020; 142: 3532 12o Mehta MM, Boit TB, Dander JE, Garg NK. Org. Lett. 2020; 22: 1 ; Knochel, P.; Kremsmair, A. Synfacts 2020, 16, 49 12p Watanabe E, Chen Y, May O, Ley SV. Chem. Eur. J. 2020; 26: 186 ; Knochel, P.; Skotnitzki, J. Synfacts 2020, 16, 240 12q Lévêque C, Ollivier C, Fensterbank L. Nickel Catalysis in Organic Synthesis: Methods and Reactions 2020; 151 12r McGuire RT, Simon CM, Yadav AA, Ferguson MJ, Stradiotto M. Angew. Chem. Int. Ed. 2020; 59: 8952 12s Pulikottil FT, Pilli R, Suku RV, Rasappan R. Org. Lett. 2020; 22: 2902 13a Kianmehr E, Amiri Lomedasht Y, Faghih N, Khan KM. J. Org. Chem. 2016; 81: 6087 13b Kianmehr E, Faghih N, Tanbakouchian A, Mahdavi M. Eur. J. Org. Chem. 2016; 4269 13c Kianmehr E, Nasab SB. Eur. J. Org. Chem. 2018; 6447 14a John A, Nicholas KM. J. Org. Chem. 2012; 77: 5600 14b Sun X, Sun Y, Zhang C, Rao Y. Chem. Commun. 2014; 50: 1262 14c Uhlig N, Li CJ. Chem. Eur. J. 2014; 20: 12066 14d Yang X, Sun Y, Chen Z, Rao Y. Adv. Synth. Catal. 2014; 356: 1625 14e Seth K, Nautiyal M, Purohit P, Parikh N, Chakraborti AK. Chem. Commun. 2015; 51: 191 14f Sun X, Yao X, Zhang C, Rao Y. Chem. Commun. 2015; 51: 10014 14g Tanaka J, Shibata Y, Joseph A, Nogami J, Terasawa J, Yoshimura R, Tanaka K. Chem. Eur. J. 2020; 26: 5774 15a Armstrong VC, Farlow DW, Moodie RB. J. Chem. Soc. B 1968; 1099 15b Dittert LW, Higuchi T. J. Pharm. Sci. 1963; 52: 852 15c Norberto FP, Santos SP, Iley J, Silva DB, Corte Real M. J. Braz. Chem. Soc. 2007; 18: 171 15d Parkhomenko PI, Rybakova MV, Bezmenova T, Zaika TD. Chem. Heterocycl. Compd. 1980; 16: 1122 15e Vontor T, Večeřa M. Collect. Czech. Chem. Commun. 1973; 38: 516 16 Fosu SC, Hambira CM, Chen AD, Fuchs JR, Nagib DA. Chem 2019; 5: 417 17 Wippert NA, Jung N, Bräse S. ACS Comb. Sci. 2019; 21: 568 18 Hirose Y, Yamazaki M, Nogata M, Nakamura A, Maegawa T. J. Org. Chem. 2019; 84: 7405 19 Wasilewska A, Woźniak BA, Doridot G, Piotrowska K, Witkowska N, Retailleau P, Six Y. Chem. Eur. J. 2013; 19: 11759 20 Matsuhira T, Yamamoto H, Okamura T.-a, Ueyama N. Org. Biomol. Chem. 2008; 6: 1926 21 Yan JX, Li H, Liu XW, Shi JL, Wang X, Shi ZJ. Angew. Chem. Int. Ed. 2014; 53: 4945 22 Iida K, Ishida S, Watanabe T, Arai T. J. Org. Chem. 2019; 84: 7411 23 Rasheed S, Rao DN, Reddy AS, Shankar R, Das P. RSC Adv. 2015; 5: 10567 24 Shang J, Si W, Zhao W, Che Y, Hou J.-L, Jiang H. Org. Lett. 2014; 16: 4008 25 Houlden CE, Lloyd-Jones GC, Booker-Milburn KI. Org. Lett. 2010; 12: 3090 26 Xu N, Li D, Zhang Y, Wang L. Org. Biomol. Chem. 2015; 13: 9083 27 Denis JG, Franci G, Altucci L, Aurrecoechea JM, de Lera ÁR, Álvarez R. Org. Biomol. Chem. 2015; 13: 2800 28 Kadnikov DV, Larock RC. J. Org. Chem. 2004; 69: 6772 Supplementary Material Supplementary Material Supporting Information
