Synthesis 2020; 52(16): 2311-2329
DOI: 10.1055/s-0040-1707115
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Triarylmethane Synthesis

Xue Liu
,
Xiangmei Wu
,
Ling Zhang
,
Xiaoyan Lin
,
We thank the Natural Science Foundation of Zhejiang Province (LQ18B020001) for financial support.
Further Information

Publication History

Received: 23 March 2020

Accepted after revision: 08 April 2020

Publication Date:
14 May 2020 (online)


Abstract

Triarylmethanes are important molecules in organic chemistry. This review discusses advances in their synthesis summarized in five categories according to the starting materials: (1) benzyl reagents with different leaving groups, such as benzyl alcohols, ethers, esters, phosphates, sulfones, thioethers, sulfonamide, 1,3-dicarbonyls, and ammonium salts; (2) reactions via para- or ortho-quinone methides; (3) arylation of benzyl halides; (4) C–H activation of methylenes; and (5) reactions of aldehydes or N-tosylhydrazones. Triarylmethane derivatives such as 9-arylxanthenones, 9-arylfluorenes, and aryloxepines are also discussed.

1 Introduction

2 Benzyl Reagents with Leaving Groups

3 Quinone Methide Mediated Reactions

4 Arylation of Benzyl Halides

5 C–H Activation of Methylene

6 Reactions of Carbonyl Compounds

7 Conclusions

 
  • References

    • 1a Shchepinov MS, Korshun VA. Chem. Soc. Rev. 2003; 32: 170
    • 1b Nair V, Thomas S, Mathew SC, Abhilash KG. Tetrahedron 2006; 62: 6731
    • 1c Mondal S, Panda G. RSC Adv. 2014; 4: 28317
    • 1d Dothager RS, Putt KS, Allen BJ, Hergenrother PJ. J. Am. Chem. Soc. 2008; 130: 10274
    • 1e Chen C, Chiou C, Chen GS, Chen S, Hu C, Chi W, Chu Y, Hwang L, Chen P, Chen D, Liaw S, Chern J. J. Med. Chem. 2009; 52: 2716
    • 1f Zheng ZP, Zhang YN, Zhang S, Chen J. Bioorg. Med. Chem. Lett. 2016; 26: 795
    • 1g Singh P, Manna SK, Jana AK, Saha T, Mishra P, Bera S, Parai MK, Kumar MS. L, Mondal S, Trivedi P, Chaturvedi V, Singh S, Sinha S, Panda G. Eur. J. Med. Chem. 2015; 95: 357
    • 1h Mason CD, Nord FF. J. Org. Chem. 1951; 16: 722
    • 1i Ghaisas VV, Kane BJ, Nord FF. J. Org. Chem. 1958; 23: 560
    • 1j Irie M. J. Am. Chem. Soc. 1983; 105: 2078
    • 1k Duxbury DF. Chem. Rev. 1993; 93: 381
    • 1l Nakagawa S, Sakakibara K, Gotoh H. Dyes Pigm. 2016; 124: 130
    • 1m Miura T, Urano Y, Tanaka K, Nagano T, Ohkubo K, Fukuzumi S. J. Am. Chem. Soc. 2003; 125: 8666
    • 1n Urano Y, Kamiya M, Kanda K, Ueno T, Hirose K, Nagano T. J. Am. Chem. Soc. 2005; 127: 4888
    • 1o Abe H, Wang J, Furukawa K, Oki K, Uda M, Tsuneda S, Ito Y. Bioconjugate Chem. 2008; 19: 1219
    • 2a Thirupathi P, Kim SS. Tetrahedron 2010; 66: 2995
    • 2b Gao J, Wang J.-Q, Song Q.-W, He L.-N. Green Chem. 2011; 13: 1182
    • 2c Teranishi S, Kurahash T, Matsubara S. Synlett 2013; 24: 2148
    • 2d Cullen A, Muller AJ, Bradley D, Williams G. RSC Adv. 2017; 7: 42168
    • 2e Rafiee E, Jalilian F. Lett. Org. Chem. 2014; 11: 203
    • 2f Desroches J, Champagne PA, Benhassine Y, Paquin JF. Org. Biomol. Chem. 2015; 13: 2243
    • 2g Barbero M, Cadamuro S, Dughera S, Rucci M, Spano G, Venturello P. Tetrahedron 2014; 70: 1818
    • 2h Sato Y, Aoyama T, Takido T, Kodomari M. Tetrahedron 2014; 68: 7077
    • 2i Yang GP, Dilixiati D, Yang T, Liu D, Yu B, Hu C. Appl. Organomet. Chem. 2018; 32: 4450
    • 2j Meng SS, Wang Q, Huang GB, Lin LR, Zhao JL, Chan AS. C. RSC Adv. 2018; 8: 30946
    • 3a Hikawa H, Suzuki H, Azumaya I. J. Org. Chem. 2013; 78: 12128
    • 3b Hirashita T, Kuwahara S, Okochi S, Tsuji M, Araki S. Tetrahedron Lett. 2010; 51: 1847
    • 4a Hikawa H, Suzuki H, Yokoyama Y, Azumaya I. J. Org. Chem. 2013; 78: 6714
    • 4b Nallagonda R, Rehan M, Ghorai P. J. Org. Chem. 2014; 79: 2934
    • 4c Li Y, Zhu Y, Tu G, Zhang J, Zhao Y. RSC Adv. 2018; 8: 30374
    • 5a Suzuki N, Tsuchihashi S, Nakata K. Tetrahedron Lett. 2016; 57: 1456
    • 5b Yaragorla S, Saini PL, Babu PV, Almansour AI, Arumugam N. Tetrahedron Lett. 2016; 57: 2351
    • 6a Xu X, Li T, Li X, Shao J. Synlett 2013; 24: 383
    • 6b Das SK, Singh R, Panda G. Eur. J. Org. Chem. 2009; 4757
    • 7a Ciszek B, Fleischer L. Chem. Eur. J. 2018; 24: 12259
    • 7b Kasner G, Boucher-Jacobs C, McClain JM, Nicholas KM. Chem. Commun. 2016; 52: 7257
    • 7c Sai M. Adv. Synth. Catal. 2018; 360: 4330
    • 7d Tandiary MA, Masui Y, Onaka M. Tetrahedron Lett. 2014; 55: 4160
    • 7e Matsumoto S, Naito M, Oseki T, Akazome M, Otani Y. Tetrahedron 2017; 73: 7254
    • 7f Tian Y, Uchida K, Kurata H, Hirao Y, Nishiuchi T, Kubo T. J. Am. Chem. Soc. 2014; 136: 12784
  • 8 Too PC, Chan GH, Tnay YL, Hirao H, Chiba S. Angew. Chem. Int. Ed. 2016; 55: 3719
    • 9a Taylor BL. H, Harris MR, Jarvo ER. Angew. Chem. Int. Ed. 2012; 51: 7790
    • 9b Li Y, Xiong Y, Li X, Ling X, Huang R, Zhang X, Yang J. Green Chem. 2014; 16: 2976
    • 10a Zhou Q, Srinivas HD, Dasgupta S, Watson MP. J. Am. Chem. Soc. 2013; 135: 3307
    • 10b Chen Q, Fan X, Zhang L, Yang L. RSC Adv. 2015; 5: 15338
    • 10c Harris MR, Hanna LE, Greene MA, Moore CE, Jarvo ER. J. Am. Chem. Soc. 2013; 135: 3303
  • 11 Pallikonda G, Chakravarty M. J. Org. Chem. 2016; 81: 2135
    • 12a Nambo M, Ariki ZT, Daniel CG, Beattie DD, Crudden CM. Org. Lett. 2016; 18: 2339
    • 12b Das B, Reddy CR, Sindhu C, Sudhakar C, Nagendra S. Synthesis 2010; 3731
    • 12c Nambo M, Crudden CM. Angew. Chem. Int. Ed. 2014; 53: 742
    • 12d Nambo M, Yim JC.-H, Fowler KG, Crudden CM. Synlett 2017; 28: 2936
  • 13 Lanzi M, Merad J, Boyarskaya DV, Maestri G, Allain C, Masson G. Org. Lett. 2018; 20: 5247
    • 14a Thirupathi P, Kim SS. J. Org. Chem. 2010; 75: 5240
    • 14b Huang D, Wang X, Wang X, Chen W, Wang X, Hu Y. Org. Lett. 2016; 18: 604
    • 14c Huang D, Yang W, Zhang J, Wang X, Wang X, Hu Y. RSC Adv. 2016; 6: 47570
    • 14d Huang D, Wang X, Wang X, Zhang J, Wang X, Hu Y. J. Mol. Catal. A: Chem. 2016; 423: 185
    • 14e Li H, Li W, Liu W, He Z, Li Z. Angew. Chem. Int. Ed. 2011; 50: 2975
    • 14f Paul D, Khatua S, Chatterjee PN. New J. Chem. 2019; 43: 10056
    • 14g Aoyama T, Kubota S, Ogawa S, Nakajima E, Mitsuyama E, Iwabuch T, Kaneko H, Obara R, Takido T, Kodomari M, Ouchi A. Synthesis 2015; 47: 2945
    • 15a Zhang Z, Wang H, Qiu N, Kong Y, Zeng W, Zhang Y, Zhao J. J. Org. Chem. 2018; 83: 8710
    • 15b Shacklady-McAtee DM, Roberts YK. M, Basch CH, Song Y, Watson MP. Tetrahedron 2014; 70: 4257
    • 16a Zhou T, Li S, Huang B, Li C, Zhao Y, Chen J, Chen A, Xiao Y, Liu L, Zhang J. Org. Biomol. Chem. 2017; 15: 4941
    • 16b Singh G, Goswami P, Anand RV. Org. Biomol. Chem. 2018; 16: 384
    • 16c Mondal S, Roy D, Jaiswal MK, Panda G. Tetrahedron Lett. 2018; 59: 89
    • 16d Wu Q, Li G, Yang S, Shi X, Huang T, Du X, Chen Y. Org. Biomol. Chem. 2019; 17: 3462
    • 16e Saha S, Alamsetti SK, Schneider C. Chem. Commun. 2015; 51: 1461
    • 16f Huang Y, Hayashi T. J. Am. Chem. Soc. 2015; 137: 7556
    • 16g Wang Y, Zhang C, Wang H, Jiang Y, Du X, Xu D. Adv. Synth. Catal. 2017; 359: 791
    • 16h Dada R, Singh G, Pareek A, Kausar S, Yaragorla S. Tetrahedron Lett. 2016; 57: 3739
    • 16i Jiang B, Liu S, Chen K, Lan X, Hao W, Li G, Tu S. Chem. Commun. 2017; 53: 10692
    • 17a Huang R, Zhang X, Pan J, Li J, Shen H, Ling X, Xiong Y. Tetrahedron 2015; 71: 1540
    • 17b Watanabe N, Matsugi A, Nakano K, Ichikawa Y, Kotsuki H. Synlett 2014; 25: 438
    • 17c Mesa JA, Velázquez-Palenzuela A, Brillas E, Torres JL, Juliá L. Tetrahedron 2011; 67: 3119
    • 17d López-Pérez A, Adrio J, Carretero JC. Org. Lett. 2009; 11: 5514
    • 17e Tao C, Sun L, Wang B, Liu Z, Zhai YQ, Zhang XL. Tetrahedron Lett. 2017; 58: 305
    • 17f Saha T, Kumar MS. L, Bera S, Karkara BB, Panda G. RSC Adv. 2017; 7: 6966
    • 17g Sun Y, Yi J, Lu X, Zhang Z, Xiao B, Fu Y. Chem. Commun. 2014; 50: 11060
    • 17h Chandrasekhar V, Narayanan RS, Thilagar P. Organometallics 2009; 28: 5883
    • 17i Jin L, Wei W, Sun N, Hu B, Shen Z, Hu X. Org. Chem. Front. 2018; 5: 2484
    • 17j Matthew SC, Glasspoole BW, Eisenberger P, Crudden CM. J. Am. Chem. Soc. 2014; 136: 5828
    • 18a Ali M, Liu L.-P, Hammond GB, Xu B. Tetrahedron Lett. 2009; 50: 4078
    • 18b Zhu J, Pérez M, Caputo CB, Stephan DW. Angew. Chem. Int. Ed. 2016; 55: 1417
    • 19a Li J, Wu C, Zhou BH, Walsh PJ. J. Org. Chem. 2018; 83: 2993
    • 19b Ji X, Huang T, Wu W, Liang F, Cao S. Org. Lett. 2015; 17: 5096
    • 19c Zhang J, Bellomo A, Trongsiriwat N, Jia T, Carroll PJ, Dreher SD, Tudge MT, Yin HL, Robinson JR, Schelter EJ, Walsh PJ. J. Am. Chem. Soc. 2014; 136: 6276
    • 19d Zhang J, Bellomo A, Creamer AD, Dreher SD, Walsh PJ. J. Am. Chem. Soc. 2012; 134: 13765
    • 19e Chen J.-J, Onogi S, Hsieh Y.-C, Hsiao C.-C, Higashibayashi S, Sakurai H, Wu Y.-T. Adv. Synth. Catal. 2012; 354: 1551
    • 19f Ji Y.-Y, Lu L.-L, Shi Y.-C, Shao L.-X. Org. Biomol. Chem. 2014; 12: 8488
  • 20 Mylavarapu S, Yadav M, Bhanuchandra M. Org. Biomol. Chem. 2018; 16: 7815
    • 21a Li Y.-Z, Li B.-J, Lu X.-Y, Lin S, Shi Z.-J. Angew. Chem. Int. Ed. 2009; 48: 3817
    • 21b Storr TE, Teskey CJ, Greaney MF. Chem. Eur. J. 2016; 22: 18169
    • 21c Okajima M, Soga K, Watanabe T, Terao K, Nokami T, Suga S, Yoshida J.-I. Bull. Chem. Soc. Jpn. 2009; 82: 594
    • 21d Wu H, Su CL, Tandiana R, Liu C, Qiu C, Bao Y, Wu JE, Xu YS, Lu J, Fan DY, Loh KP. Angew. Chem. Int. Ed. 2018; 57: 10848
    • 21e Pinter A, Klussmann M. Adv. Synth. Catal. 2012; 354: 701
    • 22a Wang X, Yu D.-G, Glorius F. Angew. Chem. Int. Ed. 2015; 54: 10280
    • 22b Zhang W, Chen P, Liu G. J. Am. Chem. Soc. 2017; 139: 7709
    • 22c Zhang W, Wu L, Chen P, Liu G. Angew. Chem. Int. Ed. 2019; 58: 6425
    • 23a Liang D, Li J, Li Y, Wang BL, Cheng P, Luo S. Synth. Commun. 2016; 46: 379
    • 23b Xu C, Yuan H, Liu Y, Wang M, Liu Q. RSC Adv. 2014; 4: 1559
    • 23c Tong J, Yang C, Xu D.-z. Synthesis 2016; 48: 3559
    • 24a Chaudhary GR, Bansal P, Kaur N, Mehta SK. RSC Adv. 2014; 4: 49462
    • 24b Soleimani E, Zainali M, Lotfi S. Lett. Org. Chem. 2011; 8: 573
    • 24c Rao GB. D, Kaushik MP, Halve AK. Tetrahedron Lett. 2012; 53: 2741
    • 24d Zolfigol MA, Moosavi-Zare AR, Arghavani-Hadi P, Zare A, Khakyzadeh V, Darvishi G. RSC Adv. 2012; 2: 3618
    • 24e Kumar R, Nandi GC, Verma RK, Singh MS. Tetrahedron Lett. 2010; 51: 442
    • 24f Fekri LZ, Nikpassand M, Fard HS, Marvi O. Lett. Org. Chem. 2016; 13: 135
    • 24g Sashidhara KV, Kumar A, Dodda RP, Kumar B. Tetrahedron Lett. 2012; 53: 3281
    • 24h Wu L, Yang C, Yang L, Yang L. Phosphorus, Sulfur Silicon Relat. Elem. 2010; 185: 903
    • 24i Shaterian HR, Doostmohammadi R, Khorami F, Ghashang M. Phosphorus, Sulfur Silicon Relat. Elem. 2010; 185: 171
    • 25a Ganesan SS, Rajendran N, Sundarakumar SL, Ganesan A, Pemiah B. Synthesis 2013; 45: 1564
    • 25b Davod F, Kiasat AR, Enjilzadeh M, Cheraghchi M. Lett. Org. Chem. 2016; 13: 58
    • 25c Karimi AR, Dalirnasab Z, Karimi M. Synthesis 2014; 46: 917
    • 25d Mirkhani V, Moghadam M, Tangestaninejad S, Mohammadpoor-Baltork I, Mahdavi M. Synth. Commun. 2009; 39: 4328
    • 25e Liu Y.-H, Tao X.-Y, Lei L.-Q, Zhang Z.-H. Synth. Commun. 2009; 39: 580
    • 25f Patil MS, Palav AV, Khatri CK, Chaturbhuj GU. Tetrahedron Lett. 2017; 58: 2859
    • 25g Shomali A, Valizadeh H, Banan A, Rahim MR. RSC Adv. 2015; 5: 88202
    • 26a Wu H, Chen X.-M, Wan Y, Xin H.-Q, Xu H.-H, Yue C.-H, Pang L.-L, Ma R. Synth. Commun. 2009; 39: 3762
    • 26b Dutta AK, Gogoi P, Borah R. RSC Adv. 2014; 4: 41287
    • 26c Shirini F, Abedini M, Seddighi M, Jolodar OG, Safarpoor M, Langroodi N, Zamani S. RSC Adv. 2014; 4: 63526
    • 26d Hajipour AR, Ghayeb Y, Sheikhan N, Ruoho AE. Synlett 2010; 741
    • 26e Zhu A, Bai S, Jin W, Liu R, Li L, Zhao Y, Wang J. RSC Adv. 2014; 4: 36031
    • 26f Kusampally U, Pagadala R, Kamatala CR. Tetrahedron Lett. 2017; 58: 3316
    • 26g Ghasemnejad-Bosra H, Forouzani M. Heterocycl. Commun. 2011; 17: 83
    • 27a Naeimi H, Golestanzadeh M. RSC Adv. 2014; 4: 56475
    • 27b Naeimi H, Golestanzadeh M. New J. Chem. 2015; 39: 2697
    • 27c Fareghi-Alamdari R, Golestanzadeh AM, Agend F, Zekri N. Can. J. Chem. 2013; 91: 982
    • 27d Vidyasagar N, Nanda R, Mangal R, Kathiravan MK. Synth. Commun. 2012; 42: 3157
    • 28a Gomes RF. A, Coelho JA. S, Frade RF. M, Trindade AF. C, Afonso AM. J. Org. Chem. 2015; 80: 10404
    • 28b Bachhav HM, Takale BS, Telvekar VN. Synth. Commun. 2013; 43: 1909
    • 28c Mukhopadhyay C, Datta A, Tapaswi PK. Synth. Commun. 2012; 42: 2453
    • 28d Chaudhari AS, Parab YS, Patil V, Sekar N, Shukla SR. RSC Adv. 2012; 2: 12112
    • 28e Zhang G, Ma N, Jiang B, Shi F, Tu S.-J. Synthesis 2010; 3993
    • 29a Mohammadiannejad-Abbasabadi K, Mohammadpoor-Baltork I, Tangestaninejad S, Moghadam M, Mirkhani V, Kia R. Tetrahedron 2016; 72: 1433
    • 29b Genovese S, Epifano F, Pelucchini C, Curini M. Eur. J. Org. Chem. 2009; 1132
    • 29c Pratihar S. Org. Biomol. Chem. 2016; 14: 2854
    • 29d Maity AK, Bhattacharjee M, Roy S. J. Organomet. Chem. 2014; 768: 42
    • 29e Wang A, Xing P, Zheng X, Cao H, Yang G, Zheng X. RSC Adv. 2015; 5: 59022
    • 29f Jaratjaroonphong J, Sathalalai S, Techasauvapak P, Reutrakul V. Tetrahedron Lett. 2009; 50: 6012
    • 29g Babu BM, Thakur PB, Rao NN, Kumar GS, Meshram HM. Tetrahedron Lett. 2014; 55: 1868
    • 29h Prakash GK. S, Panja C, Shakhmin A, Shah E, Mathew T, Olah GA. J. Org. Chem. 2009; 74: 8659
    • 29i Chandrasekhar S, Khatun S, Rajesh G, Reddy CR. Tetrahedron Lett. 2009; 50: 6693
    • 29j Wilsdorf M, Leichnitz D, Reissig H.-U. Org. Lett. 2013; 15: 2494
    • 29k Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadiannejad-Abbasabadi K, Khavasi HR. Eur. J. Org. Chem. 2011; 1357
    • 29l Barbero M, Cadamuro S, Dughera S, Magistris C, Venturello P. Org. Biomol. Chem. 2011; 9: 8393
    • 29m Mohammadiannejad K, Ranjbar-Karimi R, Haghighat F. New J. Chem. 2019; 43: 5543
    • 29n Leng Y, Chen F, Zuo L, Duan W. Tetrahedron Lett. 2010; 51: 2370
  • 30 Kothandapani J, Ganesan A, Vairaprakash P, Ganesan SS. Tetrahedron Lett. 2015; 56: 2238
    • 31a Babu BM, Thakur PB, Bangade VM, Meshram HM. Tetrahedron Lett. 2015; 56: 766
    • 31b Wang X, Chen M, Xie F, Zhang M. RSC Adv. 2014; 4: 14744
    • 32a Reddy CR, Ramesh P, Rao NN, Ali SA. Eur. J. Org. Chem. 2011; 2133
    • 32b Singh R, Panda G. Org. Biomol. Chem. 2010; 8: 1097
    • 32c Li H, Yang J, Liu Y, Li Y. J. Org. Chem. 2009; 74: 6797
    • 32d Li Q, Xu W, Hu J, Chen X, Zhang F, Zheng H. RSC Adv. 2014; 4: 27722
    • 32e Das D, Pratihar S, Roy S. Org. Lett. 2012; 14: 4870
    • 32f Wang S.-G, Han L, Zeng M, Sun F.-L, Zhang W, You S.-L. Org. Biomol. Chem. 2012; 10: 3202
    • 32g Das T, Chakraborty A, Sarkar A. Tetrahedron Lett. 2014; 55: 5174
  • 33 Chinta BS, Baire B. Tetrahedron Lett. 2016; 57: 5381
  • 34 Luo Y, Wu J. Chem. Commun. 2010; 46: 3785
    • 35a Kumar GS, Kumar AS, Swetha A, Babu BM, Meshram HM. Synlett 2015; 27: 631
    • 35b Qiao C, Liu X.-F, Fu H.-C, Yang H.-P, Zhang Z.-B, He L.-N. Chem. Asian J. 2018; 13: 2664
    • 36a Xia Y, Hu F, Liu Z, Qu P, Ge R, Ma C, Zhang Y, Wang J. Org. Lett. 2013; 15: 1784
    • 36b Xia Y, Hu F, Xia Y, Liu Z, Ye F, Zhang Y, Wang J. Synthesis 2017; 49: 1073
    • 36c Xu S, Wu G, Ye F, Wang X, Li H, Zhao X, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2015; 54: 4669
    • 36d Liu Z, Tan H, Wang L, Fu T, Xia Y, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2015; 54: 3056
    • 36e Shen X, Gu N, Liu P, Ma X, Xie J, Yan L, He L, Dai B. RSC Adv. 2015; 5: 63726