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SCIENTIA SINICA Chimica, Volume 50 , Issue 5 : 526-551(2020) https://doi.org/10.1360/SSC-2019-0174

Recent advances in methylating agents

More info
  • ReceivedDec 31, 2019
  • AcceptedFeb 29, 2020
  • PublishedApr 26, 2020

Abstract


Funded by

国家自然科学基金(21972064,21901111)

江苏省自然科学基金(BK20170632)


References

[1] Jones PA, Takai D. Science, 2001, 293: 1068-1070 CrossRef PubMed Google Scholar

[2] Zhang L, Ding X, Cui J, Xu H, Chen J, Gong YN, Hu L, Zhou Y, Ge J, Lu Q, Liu L, Chen S, Shao F. Nature, 2012, 481: 204-208 CrossRef PubMed Google Scholar

[3] Roundtree IA, Evans ME, Pan T, He C. Cell, 2017, 169: 1187-1200 CrossRef PubMed Google Scholar

[4] Harcourt EM, Kietrys AM, Kool ET. Nature, 2017, 541: 339-346 CrossRef PubMed ADS Google Scholar

[5] Barreiro EJ, Kümmerle AE, Fraga CAM. Chem Rev, 2011, 111: 5215-5246 CrossRef PubMed Google Scholar

[6] Schönherr H, Cernak T. Angew Chem Int Ed, 2013, 52: 12256-12267 CrossRef PubMed Google Scholar

[7] Jaenisch R, Bird A. Nat Genet, 2003, 33: 245-254 CrossRef PubMed Google Scholar

[8] Okano M, Bell DW, Haber DA, Li E. Cell, 1999, 99: 247-257 CrossRef Google Scholar

[9] Choy JS, Wei S, Lee JY, Tan S, Chu S, Lee TH. J Am Chem Soc, 2010, 132: 1782-1783 CrossRef PubMed Google Scholar

[10] Ullmann F. Justus Liebigs Ann Chem, 1903, 104–124. Google Scholar

[11] Pschorr R, Dickhäuser F. Ber Dtsch Chem Ges, 1911, 44: 2633-2640 CrossRef Google Scholar

[12] Perkin WH, Weizmann C. J Chem Soc Trans, 1906, 89: 1649-1665 CrossRef Google Scholar

[13] Walden P. Ber Dtsch Chem Ges, 1907, 40: 3214-3217 CrossRef Google Scholar

[14] Riiber CN. Ber Dtsch Chem Ges, 1915, 48: 823-831 CrossRef Google Scholar

[15] Houben J, Brassert W. Ber Dtsch Chem Ges, 1906, 39: 3233-3240 CrossRef Google Scholar

[16] Diels O, Gollmann R. Ber Dtsch Chem Ges, 1912, 44: 3158-3165 CrossRef Google Scholar

[17] Germuth FG. J Am Chem Soc, 1929, 51: 1555-1557 CrossRef Google Scholar

[18] Smith LI. Org Synth, 1931, 11: 66-69 CrossRef Google Scholar

[19] Gschwend HW, Rodriguez HR. Organic Reactions. Oxford: Wiley, 1979. 1–360. Google Scholar

[20] Paquette LA, Burke LD. J Org Chem, 1987, 52: 2674-2679 CrossRef Google Scholar

[21] Mitchell TN, Wickenkamp R, Amamria A, Dicke R, Schneider U. J Org Chem, 1987, 52: 4868-4874 CrossRef Google Scholar

[22] Shiner CS, Tsunoda T, Goodman BA, Ingham S, Lee SH, Vorndam PE. J Am Chem Soc, 1989, 111: 1381-1392 CrossRef Google Scholar

[23] Wang Y, Xia J, Wang Q. Am J Ind Med, 1988, 13: 455-462 CrossRef PubMed Google Scholar

[24] Hwu JR, Tseng WN, Gnabre J, Giza P, Huang RCC. J Med Chem, 1998, 41: 2994-3000 CrossRef PubMed Google Scholar

[25] Banerjee A, Grewer C, Ramakrishnan L, Jäger J, Gameiro A, Breitinger HGA, Gee KR, Carpenter BK, Hess GP. J Org Chem, 2003, 68: 8361-8367 CrossRef PubMed Google Scholar

[26] Müller DS, Untiedt NL, Dieskau AP, Lackner GL, Overman LE. J Am Chem Soc, 2015, 137: 660-663 CrossRef PubMed Google Scholar

[27] Nie W, Gong J, Chen Z, Liu J, Tian D, Song H, Liu XY, Qin Y. J Am Chem Soc, 2019, 141: 9712-9718 CrossRef PubMed Google Scholar

[28] Mouselmani R, Da Silva E, Lemaire M. Tetrahedron, 2015, 71: 8905-8910 CrossRef Google Scholar

[29] AlderR W, Phillips JGE, Huang L, Huang X. Methyltrifluorometha-nesulfonatein Encyclopedia of Reagents for Organic Synthesis. Hoboken: Wiley, 2005. 1–9. Google Scholar

[30] Jolly D, Lakhrissi Y, Kovacevic MM, Chertkow H, Schirrmacher R. J Label Compd Radiopharm, 2007, 50: 1230-1233 CrossRef Google Scholar

[31] Stang PJ, Hanack M, Subramanian LR. Chemischer Infsdienst, 1982, 13: 85-126 CrossRef Google Scholar

[32] Liang Z, Xue W, Lin K, Gong H. Org Lett, 2014, 16: 5620-5623 CrossRef PubMed Google Scholar

[33] Wang J, Zhao J, Gong H. Chem Commun, 2017, 53: 10180-10183 CrossRef PubMed Google Scholar

[34] Smith RT, Zhang X, Rincón JA, Agejas J, Mateos C, Barberis M, García-Cerrada S, de Frutos O, MacMillan DWC. J Am Chem Soc, 2018, 140: 17433-17438 CrossRef PubMed Google Scholar

[35] Catellani M, Frignani F, Rangoni A. Angew Chem Int Ed Engl, 1997, 36: 119-122 CrossRef Google Scholar

[36] Gao Q, Shang Y, Song F, Ye J, Liu ZS, Li L, Cheng HG, Zhou Q. J Am Chem Soc, 2019, 141: 15986-15993 CrossRef PubMed Google Scholar

[37] Aricò F, Tundo P. Russ Chem Rev, 2010, 79: 479-489 CrossRef ADS Google Scholar

[38] Huang S, Yan B, Wang S, Ma X. Chem Soc Rev, 2015, 44: 3079-3116 CrossRef PubMed Google Scholar

[39] Fiorani G, Perosa A, Selva M. Green Chem, 2018, 20: 288-322 CrossRef Google Scholar

[40] Tundo P, Selva M. Acc Chem Res, 2002, 35: 706-716 CrossRef PubMed Google Scholar

[41] Tundo P, Selva M, Memoli S. ACS Symp Ser, 2000, 767: 87–99. Google Scholar

[42] Tundo P, Musolino M, Aricò F. Green Chem, 2018, 20: 28-85 CrossRef Google Scholar

[43] Shieh WC, Dell S, Repič O. Org Lett, 2001, 3: 4279-4281 CrossRef PubMed Google Scholar

[44] Shieh WC, Dell S, Repič O. J Org Chem, 2002, 67: 2188-2191 CrossRef PubMed Google Scholar

[45] Rekha VV, Ramani MV, Ratnamala A, Rupakalpana V, Subbaraju GV, Satyanarayana C, Rao CS. Org Process Res Dev, 2009, 13: 769-773 CrossRef Google Scholar

[46] Jin S, Hunt AJ, Clark JH, McElroy CR. Green Chem, 2016, 18: 5839-5844 CrossRef Google Scholar

[47] Laurila ML, Magnus NA, Staszak MA. Org Process Res Dev, 2009, 13: 1199-1201 CrossRef Google Scholar

[48] Ji Y, Sweeney J, Zoglio J, Gorin DJ. J Org Chem, 2013, 78: 11606-11611 CrossRef PubMed Google Scholar

[49] Kundu SK, Mitra K, Majee A. RSC Adv, 2013, 3: 8649-8651 CrossRef Google Scholar

[50] El-Kihel A, Zouitina S, Guesmi S, Ahbala M, Bauchat P, Biersack B. Asian J Chem, 2016, 28: 1267-1269 CrossRef Google Scholar

[51] He ZT, Li H, Haydl AM, Whiteker GT, Hartwig JF. J Am Chem Soc, 2018, 140: 17197-17202 CrossRef PubMed Google Scholar

[52] Olah GA. Angew Chem, 2005, 117: 2692-2696 CrossRef Google Scholar

[53] Palo DR, Dagle RA, Holladay JD. Chem Rev, 2007, 107: 3992-4021 CrossRef PubMed Google Scholar

[54] Natte K, Neumann H, Beller M, Jagadeesh RV. Angew Chem Int Ed, 2017, 56: 6384-6394 CrossRef PubMed Google Scholar

[55] Chatterjee J, Gilon C, Hoffman A, Kessler H. Acc Chem Res, 2008, 41: 1331-1342 CrossRef PubMed Google Scholar

[56] Aurelio L, Brownlee RTC, Hughes AB. Chem Rev, 2004, 104: 5823-5846 CrossRef PubMed Google Scholar

[57] Obora Y. ACS Catal, 2014, 4: 3972-3981 CrossRef Google Scholar

[58] Yan G, Borah AJ, Wang L, Yang M. Adv Synth Catal, 2015, 357: 1333-1350 CrossRef Google Scholar

[59] Chan LKM, Poole DL, Shen D, Healy MP, Donohoe TJ. Angew Chem Int Ed, 2014, 53: 761-765 CrossRef PubMed Google Scholar

[60] Ogawa S, Obora Y. Chem Commun, 2014, 50: 2491-2493 CrossRef PubMed Google Scholar

[61] Quan X, Kerdphon S, Andersson PG. Chem Eur J, 2015, 21: 3576-3579 CrossRef PubMed Google Scholar

[62] Dang TT, Seayad AM. Adv Synth Catal, 2016, 358: 3373-3380 CrossRef Google Scholar

[63] Chakrabarti K, Maji M, Panja D, Paul B, Shee S, Das GK, Kundu S. Org Lett, 2017, 19: 4750-4753 CrossRef PubMed Google Scholar

[64] Reddy CB, Bharti R, Kumar S, Das P. ACS Sustain Chem Eng, 2017, 5: 9683-9691 CrossRef Google Scholar

[65] Siddiki SMAH, Touchy AS, Jamil MAR, Toyao T, Shimizu K. ACS Catal, 2018, 8: 3091-3103 CrossRef Google Scholar

[66] Charvieux A, Duguet N, Métay E. Eur J Org Chem, 2019, 2019(22): 3694-3698 CrossRef Google Scholar

[67] Li Y, Li H, Junge H, Beller M. Chem Commun, 2014, 50: 14991-14994 CrossRef PubMed Google Scholar

[68] Wingad RL, Bergström EJE, Everett M, Pellow KJ, Wass DF. Chem Commun, 2016, 52: 5202-5204 CrossRef PubMed Google Scholar

[69] Polidano K, Williams JMJ, Morrill LC. ACS Catal, 2019, 9: 8575-8580 CrossRef Google Scholar

[70] Schlagbauer M, Kallmeier F, Irrgang T, Kempe R. Angew Chem Int Ed, 2020, 59: 1485-1490 CrossRef PubMed Google Scholar

[71] Jin J, MacMillan DWC. Nature, 2015, 525: 87-90 CrossRef PubMed ADS Google Scholar

[72] Chen SJ, Lu GP, Cai C. RSC Adv, 2015, 5: 70329-70332 CrossRef Google Scholar

[73] Liu W, Yang X, Zhou ZZ, Li CJ. Chem, 2017, 2: 688-702 CrossRef Google Scholar

[74] McCallum T, Pitre SP, Morin M, Scaiano JC, Barriault L. Chem Sci, 2017, 8: 7412-7418 CrossRef PubMed Google Scholar

[75] Dang TT, Ramalingam B, Seayad AM. ACS Catal, 2015, 5: 4082-4088 CrossRef Google Scholar

[76] Tsarev VN, Morioka Y, Caner J, Wang Q, Ushimaru R, Kudo A, Naka H, Saito S. Org Lett, 2015, 17: 2530-2533 CrossRef PubMed Google Scholar

[77] Wang LM, Jenkinson K, Wheatley AEH, Kuwata K, Saito S, Naka H. ACS Sustain Chem Eng, 2018, 6: 15419-15424 CrossRef Google Scholar

[78] Elangovan S, Neumann J, Sortais JB, Junge K, Darcel C, Beller M. Nat Commun, 2016, 7: 12641-12648 CrossRef PubMed Google Scholar

[79] Meerwein H, Hinz G, Hofmann P, Kroning E, Pfeil E. J Prakt Chem, 1937, 147: 257-285 CrossRef Google Scholar

[80] Pichlmair S. Synlett, 2004, 195−196. Google Scholar

[81] Dai Q, Jiang Y, Yu JT, Cheng J. Synthesis, 2016, 48: 329-339 CrossRef Google Scholar

[82] Norcott PL, Hammill CL, Noble BB, Robertson JC, Olding A, Bissember AC, Coote ML. J Am Chem Soc, 2019, 141: 15450-15455 CrossRef PubMed Google Scholar

[83] Selva M, Tundo P. J Org Chem, 1998, 63: 9540-9544 CrossRef Google Scholar

[84] Ayele T, Chang SJ, Resendiz MJE. Tetrahedron Lett, 2015, 56: 4532-4536 CrossRef Google Scholar

[85] Fairley G, Hall C, Greenwood R. Synlett, 2013, 24: 570-574 CrossRef Google Scholar

[86] Janin YL, Huel C, Flad G, Thirot S. Eur J Org Chem, 2002, 2002: 1763-1769 CrossRef Google Scholar

[87] Sorribes I, Junge K, Beller M. Chem Eur J, 2014, 20: 7878-7883 CrossRef PubMed Google Scholar

[88] Zhu L, Wang LS, Li B, Li W, Fu B. Catal Sci Technol, 2016, 6: 6172-6176 CrossRef Google Scholar

[89] Qiao C, Liu XF, Liu X, He LN. Org Lett, 2017, 19: 1490-1493 CrossRef PubMed Google Scholar

[90] Pedrajas E, Sorribes I, Guillamón E, Junge K, Beller M, Llusar R. Chem Eur J, 2017, 23: 13205-13212 CrossRef PubMed Google Scholar

[91] Li JJ. Eschweiler-Clarke Reductive Alkylation of Amines. Berlin: Springer, 2009. 210–211. Google Scholar

[92] Wang Z. Eschweiler-Clarke Methylationin Comprehensive Organic Name Reactions and Reagents. Hoboken: Wiley, 2010. 1009–1012. Google Scholar

[93] Basha A, Orlando J, Weinreb SM. Synth Commun, 1977, 7: 549-552 CrossRef Google Scholar

[94] Auerbach J, Zamore MF, Weinreb SM. J Org Chem, 1976, 41: 725-726 CrossRef Google Scholar

[95] da Silva RA, Estevam IHS, Bieber LW. Tetrahedron Lett, 2007, 48: 7680-7682 CrossRef Google Scholar

[96] Ke Z, Cui X, Shi F. ACS Sustain Chem Eng, 2016, 4: 3921-3926 CrossRef Google Scholar

[97] Guyon C, Duclos MC, Métay E, Lemaire M. Tetrahedron Lett, 2016, 57: 3002-3005 CrossRef Google Scholar

[98] Nielsen DU, Hu XM, Daasbjerg K, Skrydstrup T. Nat Catal, 2018, 1: 244-254 CrossRef Google Scholar

[99] Liu XF, Li XY, Qiao C, He LN. Synlett, 2018, 29: 548-555 CrossRef Google Scholar

[100] Santoro O, Lazreg F, Minenkov Y, Cavallo L, Cazin CSJ. Dalton Trans, 2015, 44: 18138-18144 CrossRef PubMed Google Scholar

[101] Song QW, Zhou ZH, He LN. Green Chem, 2017, 19: 3707-3728 CrossRef Google Scholar

[102] Li Y, Cui X, Dong K, Junge K, Beller M. ACS Catal, 2017, 7: 1077-1086 CrossRef Google Scholar

[103] Tamura M, Miura A, Gu Y, Nakagawa Y, Tomishige K. Chem Lett, 2017, 46: 1243-1246 CrossRef Google Scholar

[104] Zhao TX, Zhai GW, Liang J, Li P, Hu XB, Wu YT. Chem Commun, 2017, 53: 8046-8049 CrossRef PubMed Google Scholar

[105] Zhang X, Wang S, Xi C. J Org Chem, 2019, 84: 9744-9749 CrossRef PubMed Google Scholar

[106] Bertilsson BM, Gustafsson B, Kühn I, Torssell K, Shimizu A. Acta Chem Scand, 1970, 24: 3590-3598 CrossRef Google Scholar

[107] Giordano C, Minisci F, Tortelli V, Vismara E. J Chem Soc Perkin Trans 2, 1984, : 293 CrossRef Google Scholar

[108] Kawai K, Li YS, Song MF, Kasai H. Bioorg Med Chem Lett, 2010, 20: 260-265 CrossRef PubMed Google Scholar

[109] O’Hagan D, Schmidberger JW. Nat Prod Rep, 2010, 27: 900 CrossRef PubMed Google Scholar

[110] Broderick JB. Nature, 2010, 465: 877-878 CrossRef PubMed ADS Google Scholar

[111] Vey JL, Drennan CL. Chem Rev, 2011, 111: 2487-2506 CrossRef PubMed Google Scholar

[112] Zhang Q, van der Donk WA, Liu W. Acc Chem Res, 2012, 45: 555-564 CrossRef PubMed Google Scholar

[113] Broderick JB, Duffus BR, Duschene KS, Shepard EM. Chem Rev, 2014, 114: 4229-4317 CrossRef PubMed Google Scholar

[114] Gui J, Zhou Q, Pan CM, Yabe Y, Burns AC, Collins MR, Ornelas MA, Ishihara Y, Baran PS. J Am Chem Soc, 2014, 136: 4853-4856 CrossRef PubMed Google Scholar

[115] Simkó DC, Elekes P, Pázmándi V, Novák Z. Org Lett, 2018, 20: 676-679 CrossRef PubMed Google Scholar

[116] Shen Z, Zhang S, Geng H, Wang J, Zhang X, Zhou A, Yao C, Chen X, Wang W. Org Lett, 2019, 21: 448-452 CrossRef PubMed Google Scholar

[117] Shi Z, Zhao Y, Wang M. Preparation method for diaryl thiophene type or diaryl sulfide type deuterated alkyl. Chinese Patent, 201810770921.4, 2018-07-13 (in Chinese) [史壮志, 赵云霏, 王敏燕. 一种二芳基并噻吩型或二芳基硫醚型氘代烷基制备方法. 中国专利, 201810770921.4, 2018-07-13]. Google Scholar

[118] De Marco R, Di Gioia ML, Liguori A, Perri F, Siciliano C, Spinella M. Tetrahedron, 2011, 67: 9708-9714 CrossRef Google Scholar

[119] Li Y, Xue D, Lu W, Wang C, Liu ZT, Xiao J. Org Lett, 2014, 16: 66-69 CrossRef PubMed Google Scholar

[120] Xia HM, Zhang FL, Ye T, Wang YF. Angew Chem Int Ed, 2018, 57: 11770-11775 CrossRef PubMed Google Scholar

[121] Uemura T, Yamaguchi M, Chatani N. Angew Chem Int Ed, 2016, 55: 3162-3165 CrossRef PubMed Google Scholar

[122] Purdie T, Irvine JC. J Chem Soc Trans, 1899, 75: 483-493 CrossRef Google Scholar

[123] Robertson GJ. J Chem Soc, 1934, 0: 330-332 CrossRef Google Scholar

[124] Liebermann C, Liebermann H. Ber Dtsch Chem Ges, 1909, 42: 1922-1930 CrossRef Google Scholar

[125] Buchman ER, Reims AO, Sargent H. J Org Chem, 1941, 06: 764-773 CrossRef Google Scholar

[126] Sundberg RL, McCloskey CM, Rees DE, Coleman GH. J Am Chem Soc, 1945, 67: 1080-1084 CrossRef Google Scholar

[127] Fones WS. J Org Chem, 1949, 14: 1099-1102 CrossRef Google Scholar

[128] Buckles RE, Mock GV. J Org Chem, 1950, 15: 680-684 CrossRef Google Scholar

[129] Helmkamp GK, Lucas HJ. J Am Chem Soc, 1952, 74: 951-954 CrossRef Google Scholar

[130] Bajusz S, Szell E, Bagdy D, Barabas E, Horvath G, Dioszegi M, Fittler Z, Szabo G, Juhasz A, Tomori E. J Med Chem, 1990, 33: 1729-1735 CrossRef PubMed Google Scholar

[131] Patel S, Waykole L, Repiĉ O, Chen KM. Synth Commun, 1996, 26: 4699-4710 CrossRef Google Scholar

[132] Boeckman RK Jr., Biegasiewicz KF, Tusch DJ, Miller JR. J Org Chem, 2015, 80: 4030-4045 CrossRef PubMed Google Scholar

[133] Toja E, Bonetti C, Butti A, Hunt P, Fortin M, Barzaghi F, Formento M, Maggioni A, Nencioni A, Galliani G. Eur J Med Chem, 1991, 26: 853-868 CrossRef Google Scholar

[134] Bolt HM, Gansewendt B. Crit Rev Toxicol, 1993, 23: 237-253 CrossRef PubMed Google Scholar

[135] Tremont SJ, Rahman HU. J Am Chem Soc, 1984, 106: 5759-5760 CrossRef Google Scholar

[136] Gooßen LJ. Appl Organom Chem, 2004, 18: 602-604 CrossRef Google Scholar

[137] Hu L, Liu X, Liao X. Angew Chem Int Ed, 2016, 55: 9743-9747 CrossRef PubMed Google Scholar

[138] Russell GA, Weiner SA. J Org Chem, 1966, 31: 248-251 CrossRef Google Scholar

[139] Maruoka K, Naganawa Y. Organoaluminum Reagents. Amsterdam: Elsevier, 2014. 49–73. Google Scholar

[140] Shang R, Ilies L, Nakamura E. Chem Rev, 2017, 117: 9086-9139 CrossRef PubMed Google Scholar

[141] Cordovilla C, Bartolomé C, Martínez-Ilarduya JM, Espinet P. ACS Catal, 2015, 5: 3040-3053 CrossRef Google Scholar

[142] Dong Z, Ye Z. Adv Synth Catal, 2014, 356: 3401-3414 CrossRef Google Scholar

[143] Zou G, Reddy YK, Falck JR. Tetrahedron Lett, 2001, 42: 7213-7215 CrossRef Google Scholar

[144] Giri R, Maugel N, Li JJ, Wang DH, Breazzano SP, Saunders LB, Yu JQ. J Am Chem Soc, 2007, 129: 3510-3511 CrossRef PubMed Google Scholar

[145] Li GX, Morales-Rivera CA, Wang Y, Gao F, He G, Liu P, Chen G. Chem Sci, 2016, 7: 6407-6412 CrossRef PubMed Google Scholar

[146] Taylor R T. Trimethylboroxine in Encyclopedia of Reagents for Organic Synthesis. Hoboken: Wiley, 2003. Google Scholar

[147] Molander GA, Yun CS, Ribagorda M, Biolatto B. J Org Chem, 2003, 68: 5534-5539 CrossRef PubMed Google Scholar

[148] St. Denis JD, Scully CCG, Lee CF, Yudin AK. Org Lett, 2014, 16: 1338-1341 CrossRef PubMed Google Scholar

[149] Jo W, Kim J, Choi S, Cho SH. Angew Chem Int Ed, 2016, 55: 9690-9694 CrossRef PubMed Google Scholar