Direct Arylation of C(sp2)–H Bonds in Anilines

Clément Jacob; Julien Annibaletto; Bert U. W. Maes; Gwilherm Evano

doi:10.1055/a-2039-7985

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(12): 1799-1823
DOI: 10.1055/a-2039-7985

review

Direct Arylation of C(sp²)–H Bonds in Anilines

Clément Jacob∗

^aLaboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université Libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/6, 1050 Brussels, Belgium

^bOrganic Synthesis Division, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium

,

Julien Annibaletto

^aLaboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université Libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/6, 1050 Brussels, Belgium

,

Bert U. W. Maes

^bOrganic Synthesis Division, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium

,

Gwilherm Evano ∗

^aLaboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université Libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/6, 1050 Brussels, Belgium

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Anilines selectively arylated at their ortho, meta or para positions are useful building blocks in synthesis and have found applications in many areas. The most straightforward method for their synthesis relies on the direct arylation of a C(sp²)–H bond of anilines, an attractive strategy avoiding the prefunctionalization of the starting anilines provided that such arylations proceed with high levels of regioselectivity. Such reactions are presented and discussed, in a comprehensive manner, in this review article, with an emphasis on the regioselectivity of the processes and factors governing both the reactivity and selectivity.

1 Introduction

2 ortho-Arylation of Anilines

2.1 Direct C(sp²)–H ortho-Arylation of Anilines

2.2 Directed C(sp²)–H ortho-Arylation of Anilines

3 meta-Arylation of Anilines

4 para-Arylation of Anilines

4.1 Direct C(sp²)–H para-Arylation of Anilines via Oxidative Radical Homodimerization

4.2 Direct C(sp²)–H para-Arylation of Anilines via Transition-Metal Catalysis

5 Conclusion and Outlook

Key words

anilines - C–H arylation - regioselectivity - catalysis - directing groups

Volltext

Referenzen

References

1a Kahl T, Schröder K.-W, Lawrence FR, Marhsall WJ, Höke H, Jäckh R. Aniline . In Ullmann’s Encyclopedia of Industrial Chemistry . Wiley-VCH; Weinheim: 2011
1b Hartwig J, Shekhar S, Shen Q, Barrios-Ianderos F. In The Chemistry of Anilines . Rappoport Z. John Wiley & Sons; Chichester: 2007
1c Schranck J, Tlili A. ACS Catal. 2018; 8: 405

2a Ragauskas AJ, Beckham GT, Biddy MJ, Chandra R, Chen F, Davis MF, Davison BH, Dixon RA, Gilna P, Keller M, Langan P, Naskar AK, Saddler JN, Tschaplinski TJ, Tuskan GA, Wyman CE. Science 2014; 344: 709
2b Becker J, Whittmann C. Biotechnol. Adv. 2019; 37: 107360
2c Blondiaux E, Bomon J, Smolén M, Kaval N, Lemière F, Sergeyev S, Diels L, Sels B, Maes BU. W. ACS Sustainable Chem. Eng. 2019; 7: 6906

3a Eicken K, Goetz N, Harreus A, Ammermann E, Lorenz G, Rang H. (BASF Aktiengesellschaft) US5480897, 1996
3b Mayer H, Golsch D, Isak H, Schröder J. (BASF Aktiengesellschaft) US7241896 B2, 2007
3c Takale BS, Thakore RR, Mallarapu R, Gallou F, Lipshutz BH. Org. Process Res. Dev. 2019; 24: 101

4a Highet RJ. J. Org. Chem. 1961; 26: 4767
4b Guo J.-J, Yang B.-J, Jing C.-X, Chen D.-Z, Hao X.-J. J. Chem. Res. 2017; 41: 202

5a Krane BD, Fagbule MO, Shamma M, Gözler B. J. Nat. Prod. 1984; 47: 1
5b Pallikonda G, Hsieh C.-Y, Su H.-L, Hsieh J.-C. Res. Chem. Intermed. 2019; 45: 5399

6a Elslager EF, Werbel LM. EP27679, 1981
6b Werbel LM, Cook PD, Elslager EF, Hung JH, Johnson JL, Kesten SJ, McNamara DJ, Ortwine DF, Worth DF. J. Med. Chem. 1986; 29: 924
6c O’Neill PM, Willock DJ, Hawley SR, Bray PG, Storr RC, Ward SA, Park BK. J. Med. Chem. 1997; 40: 437

7a Bussel JB, Cheng G, Saleh MN, Psaila B, Kovaleva L, Meddeb B, Kloczko J, Hassani H, Mayer B, Stone NL, Arning M, Provan D, Jenkins JM. N. Eng. J. Med. 2007; 357: 2237
7b Erickson-Miller CL, Jenkins J, Dickens T. WO2008073864, 2008

8 Lin JT, Chen P.-C, Yen Y.-S, Hsu Y.-C, Chou H.-H, Yeh M.-CP. Org. Lett. 2009; 11: 97

For recent review articles on the use of directing groups in C–H functionalization, see:

9a Sambiagio C, Schönbauer D, Blieck R, Dao-Huy T, Pototschnig G, Schaaf P, Wiesinger T, Farooq Zia M, Wencel-Delord J, Bessey T, Maes BU. W, Schnürch M. Chem. Soc. Rev. 2018; 47: 660
9b Jacob C, Maes BU. W, Evano G. Chem. Eur. J. 2021; 27: 13899

10 Hartwig JF, Larsen MA. ACS Cent. Sci. 2016; 2: 281
11 Sterckx H, Morel B, Maes BU. W. Angew. Chem. Int. Ed. 2019; 58: 7946
12 Monteith ER, Mampuys P, Summerton L, Clark JH, Maes BU. W, McElroy CR. Green Chem. 2020; 22: 123

For representative examples, see:

13a Franck P, Hostyn S, Dajka-Halász B, Polonka-Bálint Á, Monsieurs K, Mátyus P, Maes BU. W. Tetrahedron 2008; 64: 6030
13b Jonckers TH. M, Maes BU. W, Lemière GL. F, Rombouts G, Pieters L, Haemers A, Dommisse RA. Synlett 2003; 615
13c Liégault B, Lee D, Huestis MP, Stuart DR, Fagnou K. J. Org. Chem. 2008; 73: 5022

For recent reviews concerning visible-light photocatalysis applied to organic synthesis, see:

14a Gadde K, De Vos D, Maes BU. W. Synthesis 2023; 55: 164
14b De Vos D, Gadde K, Maes BU. W. Synthesis 2023; 55: 193

15 Ohashi M, Suwa S, Osawa Y, Tsujimoto K. J. Chem. Soc., Perkin Trans. 1 1979; 2219

16a Chen Q.-Y, Li Z.-T. J. Org. Chem. 1993; 58: 2599
16b Chen Q.-Y, Li Z.-T. J. Chem. Soc., Perkin Trans. 1 1993; 1705
16c Chen Q.-Y, Li Z.-T. J. Fluorine Chem. 1994; 66: 59

17 Marzo L, Wang S, König B. Org. Lett. 2017; 19: 5976
18 Kapoor R, Chawla R, Yadav LD. S. Tetrahedron Lett. 2019; 60: 805
19 Ghosh I, Shaikh RS, König B. Angew. Chem. Int. Ed. 2017; 56: 8544

20a Wetzel A, Ehrhardt V, Heinrich MR. Angew. Chem. Int. Ed. 2008; 47: 9130
20b Pratsch G, Wallaschkowski T, Heinrich MR. Chem. Eur. J. 2012; 18: 11555
20c Hofmann J, Gans E, Clarck T, Heinrich MR. Chem. Eur. J. 2017; 23: 9647

For literature concerning the preparation of (aryl)hydrazines, see:

21a Begtrup M, Rasmussen LK. Arylhydrazines . In Science of Synthesis . Ramsden CA, Bellus D. Georg Thieme Verlag KG; Stuttgart: 2007
21b Rademacher P. Hydrazines and Hydrazinium Salts . In Science of Synthesis . Enders D, Schaumann E. Georg Thieme Verlag KG; Stuttgart: 2009

22 Nefedov VA, German NA, Lutsenko AI, Nikishin IG. Zh. Org. Khim. 1987; 23: 172 ; J. Org. Chem. USSR (Engl. Transl.) 1987, 23, 154
23 Hofmann J, Jasch H, Heinrich MR. J. Org. Chem. 2012; 77: 10699
24 Hofmann J, Clark T, Heinrich MR. J. Org. Chem. 2016; 81: 9785

25a Hofmann J, Jasch H, Heinrich MR. J. Org. Chem. 2014; 79: 2314
25b Jiang T, Chen S.-Y, Zhuang H, Zeng R.-S, Zou J.-P. Tetrahedron Lett. 2014; 55: 4549
25c Taniguchi T, Imoto M, Takeda M, Nakai T, Mihara M, Mizuno T, Nomoto A. Synthesis 2017; 49: 1623

26 Jiang T, Chen S.-Y, Zhang G.-Y, Zeng R.-S, Zou J.-P. Org. Biomol. Chem. 2014; 12: 6922

27a Chandrasekharam M, Chiranjeevi B, Gupta KS. V, Sridhar B. J. Org. Chem. 2011; 76: 10229
27b Chiranjeevi B, Koyyada G, Prabusreenivasan S, Kumar V, Sujitha P, Kumar CG, Sridhar B, Shaik S, Chandrasekharam M. RSC Adv. 2013; 3: 16475
27c Akondi AM, Trivedi R, Sreedhar B, Kantam ML, Bhargava S. Catal. Today 2012; 198: 35
27d Berkessa SC, Clarke ZJ. F, Fotie J, Bohle DS, Grimm CC. Tetrahedron Lett. 2016; 57: 1613
27e Purtsas A, Kataeva O, Knölker H.-J. Chem. Eur. J. 2020; 26: 1499
27f Paniak TJ, Kozlowski MC. Org. Lett. 2020; 22: 1765
27g Vershinin V, Pappo D. Org. Lett. 2020; 22: 1941
27h Elsler B, Wiebe A, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Chem. Eur. J. 2015; 21: 12321

28 Barton DH. R, Finet J.-P, Giannotti C, Halley F. J. Chem. Soc., Perkin Trans. 1 1987; 241

29a Saito S, Kano T, Ohyabu Y, Yamamoto H. Synlett 2000; 1676
29b Kano T, Ohyabu Y, Saito S, Yamamoto H. J. Am. Chem. Soc. 2002; 124: 5365

30 Bardwell DA, Jeffery JC, Schatz E, Tilley EE. M, Ward MD. J. Chem. Soc. Dalton Trans 1995; 825

31a Murahashi S.-I, Yamamura M, Yanagisawa K.-I, Mita N, Kondo K. J. Org. Chem. 1979; 44: 2408
31b Xiong X, Zhu R, Huang L, Chang S, Huang J. Synlett 2017; 28: 2046

32 Pinilla C, Salamanca V, Lledós A, Albéniz AC. ACS Catal. 2022; 12: 14527

33a Ciana C.-L, Phipps RJ, Brandt JR, Meyer F.-M, Gaunt MJ. Angew. Chem. Int. Ed. 2011; 50: 458
33b Fox JC, Gilligan RE, Pitts AK, Bennett HR, Gaunt MJ. Chem. Sci. 2014; 7: 2706

34 Matsumoto K, Toubaru Y, Tachikawa S, Miki A, Sakai K, Koroki S, Hirokane T, Shindo M, Yoshida M. J. Org. Chem. 2020; 85: 15154
35 Fritsche RF, Schuh T, Kataeva O, Knölker H.-J. Chem. Eur. J. 2022; 29: e202203269
36 Odedra A, Wu C.-J, Pratap TB, Huang C.-W, Ran Y.-F, Liu R.-S. J. Am. Chem. Soc. 2005; 127: 3406

37a Pirali T, Zhang F, Miller AH, Head JL, McAusland D, Greaney MF. Angew. Chem. Int. Ed. 2012; 51: 1006
37b Mesgar M, Daugulis O. Org. Lett. 2016; 18: 3910
37c Truong T, Daugulis O. Org. Lett. 2012; 14: 5964

38 Yanagi T, Nogi K, Yorimitsu H. Chem. Eur. J. 2020; 26: 783

39a Guizzardi B, Mella M, Fagnoni M, Freccero M, Albini A. J. Org. Chem. 2001; 66: 6353
39b Guizzardi B, Mella M, Fagnoni M, Albini A. J. Org. Chem. 2003; 68: 1067

40 Guo H.-M, Li P, Niu H.-Y, Wang D.-C, Qu G.-R. J. Org. Chem. 2010; 75: 6016
41 Maiti S, Achar TK, Mal P. Org. Lett. 2017; 19: 2006

For recent review articles on the C–H functionalization of anilines, see:

42a Tischler O, Tóth B, Novák Z. Chem. Rec. 2017; 17: 184
42b Leitch JA, Frost CG. Synthesis 2018; 50: 2693

43a Kalyani D, Deprez NR, Desai LV, Sanford MS. J. Am. Chem. Soc. 2005; 127: 7330
43b Desai LV, Stowers KJ, Sanford MS. J. Am. Chem. Soc. 2008; 130: 13285
43c Deprez NR, Sanford MS. J. Am. Chem. Soc. 2009; 131: 11234

44a Daugulis O, Zaitsev VG. Angew. Chem. Int. Ed. 2005; 44: 4046
44b Shabashov D, Daugulis O. J. Org. Chem. 2007; 72: 7720

45a Zhang G.-Z, Chen C.-Q, Feng X.-H, Huang G.-S. J. Chem. Sci. 2010; 122: 149
45b Su L, Guo D.-D, Li B, Guo S.-H, Pan G.-F, Gao Y.-R, Wang Y.-Q. ChemCatChem 2017; 9: 2001
45c Sahoo K, Pradhan P, Panda N. Org. Biomol. Chem. 2020; 18: 1820

46 Haridharan R, Muralirajan K, Cheng C.-H. Adv. Synth. Catal. 2015; 357: 366
47 Li D, Xu N, Zhang Y, Wang L. Chem. Commun. 2014; 50: 14862
48 Dabiri M, Alavioon SI, Movahed SK. Eur. J. Org. Chem. 2019; 1479
49 Monzón G, Tirotta I, Knochel P. Angew. Chem. Int. Ed. 2012; 51: 10624
50 Shi Z, Li B, Wan X, Cheng J, Fang Z, Cao B, Qin C, Wang Y. Angew. Chem. Int. Ed. 2007; 46: 5554
51 Chu J.-H, Tsai S.-T, Wu M.-J. Synthesis 2009; 3757
52 Ren L, Chu W, Guan D, Hou Y, Wang M, Yuan X, Sun Z. Appl. Organomet. Chem. 2014; 28: 673

53a Chinnagolla RK, Jeganmohan M. Chem. Commun. 2014; 50: 2442
53b Hubrich J, Himmler T, Rodefeld L, Ackermann L. Adv. Synth. Catal. 2015; 357: 474

54 Yang S, Li B, Wan X, Shi Z. J. Am. Chem. Soc. 2007; 129: 6066
55 Li B.-J, Tian S.-L, Fang Z, Shi Z.-J. Angew. Chem. Int. Ed. 2008; 47: 1115
56 Brasche G, García-Fortanet J, Buchwald SL. Org. Lett. 2008; 10: 2207

57a Yeung CS, Zhao X, Borduas N, Dong VM. Chem. Sci. 2010; 1: 331
57b Yang F, Song F, Li W, Lan J, You J. RSC Adv. 2013; 3: 9649

58 Kianmehr E, Fardpour M, Kharat AN. Eur. J. Org. Chem. 2017; 3017
59 Xu H, Shang M, Dai H.-X, Yu J.-Q. Org. Lett. 2015; 17: 3830
60 Lou S.-J, Mao Y.-J, Xu D.-Q, He J.-Q, Chen Q, Xu Z.-Y. ACS Catal. 2016; 6: 3890
61 Zhu R, Lu S, Wang Q, Bai J, Wang Y, Yu Q, Huang J. Tetrahedron 2018; 74: 3879

62a Fujimoto S, Matsumoto K, Iwata T, Shindo M. Tetrahedron Lett. 2017; 58: 973
62b Zhang C, Song Y, Sang Z, Zhan L, Rao Y. J. Org. Chem. 2018; 83: 2582
62c Mei C, Zhao M, Lu W. J. Org. Chem. 2021; 86: 2714

63a Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS. J. Am. Chem. Soc. 2011; 133: 18566
63b Neufeldt SR, Sanford MS. Adv. Synth. Catal. 2012; 354: 3517

64 Jiang J, Zhang W.-M, Dai J.-J, Xu J, Xu H.-J. J. Org. Chem. 2017; 82: 3622
65 Sahoo MK, Midya SP, Landge VG, Balaraman E. Green Chem. 2017; 19: 2111
66 Mei L, Veleta JM, Gianetti TL. J. Am. Chem. Soc. 2020; 142: 12056

67a Nishikata T, Abela AR, Huang S, Lipshutz BH. J. Am. Chem. Soc. 2010; 132: 4978
67b Nishikata T, Abela AR, Huang S, Lipshutz BH. Beilstein J. Org. Chem. 2016; 12: 1040

68 Jiang P, Li F, Xu Y, Liu Q, Wang J, Ding H, Yu R, Wang Q. Org. Lett. 2015; 17: 5918

69a Nishikata T, Abela AR, Lipshutz BH. Angew. Chem. Int. Ed. 2010; 49: 781
69b Lipshutz BH, Ghorai S, Abela AR, Moser R, Nishikata T, Duplais C, Krasovskiy A, Gaston RD, Gadwood RC. J. Org. Chem. 2011; 76: 4379
69c Gabriel CM, Lee NR, Bigorne F, Klumphu P, Parmentier M, Gallou F, Lipshutz BH. J. Org. Chem. 2017; 19: 194

70 Babu SS, Shahid M, Gopinath P. Chem. Commun. 2020; 56: 5985
71 Yeung CS, Dong VM. Synlett 2011; 974
72 Uhlig N, Li C.-J. Chem. Eur. J. 2014; 20: 12066
73 Polley A, Varalaxmi K, Jana R. ACS Omega 2018; 3: 14503
74 Wan C, Zhao J, Xu M, Huang J. J. Org. Chem. 2014; 79: 4751
75 Chu J.-H, Lin P.-S, Lee Y.-M, Shen W.-T, Ming M.-J. Chem. Eur. J. 2011; 17: 13613
76 Koley M, Dastbaravardeh N, Schnürch M, Mihovilovic MD. ChemCatChem 2012; 4: 1345
77 For a general method for removal of a pyridine directing group, see: Smout V, Peschiulli A, Verbeeck S, Mitchell EA, Herrebout W, Bultinck P, Vande Velde CM. L, Berthelot D, Meerpoel L, Maes BU. W. J. Org. Chem. 2013; 78: 9803
78 Chu J.-H, Huang H.-P, Hsu W.-T, Chen S.-T, Wu M.-J. Organometallics 2014; 33: 1190
79 Miyamura S, Tsurugi H, Satoh T, Miura M. J. Organomet. Chem. 2008; 693: 2438
80 Qian C, Lin D, Deng Y, Zhang X.-Q, Jiang H, Miao G, Tang X, Zeng W. Org. Biomol. Chem. 2014; 12: 5866
81 Li M, Ye Y. ChemCatChem 2015; 7: 4137
82 Hubrich J, Himmler T, Rodefeld L, Ackermann L. ACS Catal. 2015; 5: 4089
83 Liu Z, Xian Y, Lan J, Luo Y, Ma W, You J. Org. Lett. 2019; 21: 1037
84 Reddy BV. S, Reddy CR, Reddy MR, Yarlagadda S, Sridhar B. Org. Lett. 2015; 17: 3730
85 Shao J, Chen W, Giulianotti MA, Houghten RA, Yu Y. Org. Lett. 2012; 14: 5452
86 Chary BC, Kim S, Park Y, Kim J, Lee PH. Org. Lett. 2013; 15: 2692
87 Wang P.-L, Wang Y, Li Y, Wang X.-S. Chem. Asian J. 2020; 15: 3825

88a For a review concerning meta-functionalization of arenes using palladium catalysis, see: Dey A, Agasti S, Maiti D. Org. Biomol. Chem. 2016; 14: 5440
88b For a review concerning distal C(sp²)–H functionalization of arenes, see: Dutta U, Maiti S, Bhattacharya T, Maiti D. Science 2021; 372: 701
88c For a review concerning meta- and para-selective C–H functionalization of arenes using transient mediators and non-covalent directing groups, see: Ghosh M, De Sarkar SD. Asian J. Org. Chem. 2018; 7: 1236

89 Phipps RJ, Gaunt MJ. Science 2009; 323: 1593

90a Chen B, Hou X.-L, Li Y.-X, Wu Y.-D. J. Am. Chem. Soc. 2011; 133: 7668
90b Deng C, Zhang J.-X, Lin Z. ACS Catal. 2018; 8: 2498

91 Gemoets HP. L, Laudadio G, Verstraete K, Hessel V, Noël T. Angew. Chem. Int. Ed. 2017; 56: 7161
92 Lee EY, Park J. ChemCatChem 2011; 3: 1127
93 Mathew BP, Yang HJ, Jeon H, Lee JH, Kim JC, Shin TJ, Myung K, Kwak SK, Kwak JH, Hong SY. J. Mol. Catal. A: Chem. 2016; 417: 64
94 Vásquez-Céspedes S, Holtkamp M, Karst U, Glorius F. Synlett 2017; 28: 2759

95a Catellani M, Frignani F, Rangoni A. Angew. Chem. Int. Ed. 1997; 36: 119
95b For a recent review concerning the Catellani reaction, see: Li R, Dong G. J. Am. Chem. Soc. 2020; 142: 17859

96 Wang P, Farmer ME, Huo X, Jain P, Shen P.-X, Ishoey M, Bradner JE, Wisniewski SR, Eastgate MD, Yu J.-Q. J. Am. Chem. Soc. 2016; 138: 9269
97 For a seminal example of pyridinone-type-ligand-enabled meta-C–H activation, see: Wang X.-C, Gong W, Fang L.-Z, Zhu R.-Y, Li S, Engle KM, Yu J.-Q. Nature 2015; 519: 334
98 Nakamura I, Tashiro H, Ishida Y, Terada M. Org. Lett. 2020; 22: 3794
99 For a review concerning directing-group-assisted para-C–H functionalization of arenes, see: Sasmal S, Dutta U, Lahiri GK, Maiti D. Chem. Lett. 2020; 49: 1406

100a Johnson GE, McGrane KM, Stolka M. Pure Appl. Chem. 1995; 67: 175
100b Noda T, Ogawa H, Noma N, Shirota Y. J. Mater. Chem. 1999; 9: 2177

101 Horowitz G. J. Mater. Chem. 1999; 9: 2177
102 Cariciftci NS, Smilowitz L, Heeger AJ, Wudl F. Science 1992; 258: 1474

103a Getautis V, Stanisauskaite A, Paliulis O, Uss S, Uss V. J. Prakt. Chem. 2000; 342: 58
103b Goodbrand HC, Hu N.-H. J. Org. Chem. 1999; 64: 670
103c O’Brien DF, Burrows PE, Forrest SR, Koene BE, Loy DE, Thompson ME. Adv. Mater. 1998; 10: 1108

104a Mizoguchi T, Adams RN. J. Am. Chem. Soc. 1962; 84: 2058
104b Vettorazzi N, Fernandez H, Silber JJ, Sereno L. Electrochim. Acta 1990; 35: 1081

105 Imaizumi H, Sekiguchi S, Matsui K. Bull. Chem. Soc. Jpn. 1977; 50: 948
106 Periasamy M, Jayakumar KN, Bharati P. J. Org. Chem. 2000; 65: 3548
107 Vitale P, Di Nunno L, Scilimati A. ARKIVOC 2013; (iii): 36
108 Jiang Y, Xi C, Yang X. Synlett 2005; 1381
109 Ling X, Xiong Y, Huang R, Zhang X, Zhang S, Chen C. J. Org. Chem. 2013; 78: 5218
110 Xi C, Jiang Y, Yang X. Tetrahedron Lett. 2005; 46: 3909
111 Yang X, Xi C, Jiang Y. Synth. Commun. 2006; 36: 2413
112 Kirchgessner M, Sreenath K, Gopidas KR. J. Org. Chem. 2006; 71: 9849
113 Saito T, Yoshida S, Ichikawa J. Org. Lett. 2004; 6: 4563
114 Luo M.-J, Li Y, Ouyang X.-H, Li J.-H, He D.-L. Chem. Commun. 2020; 56: 2707
115 Liu X, Cai T.-C, Guo D, Wanf B.-B, Ying S, Wang H, Tang S, Shen Q, Gui Q.-W. Tetrahedron Lett. 2021; 70: 153021
116 Lichte D, Pirkl N, Heinrich G, Dutta S, Goebel JF, Koley D, Gooßen LJ. Angew. Chem. Int. Ed. 2022; 61: e202210009
117 For a representative example of aromatic C–H functionalization promoted by thianthrenation, see: Berger F, Plutschack MB, Riegger J, Yu W, Speicher S, Ho M, Frank N, Ritter T. Nature 2019; 567: 223
118 Chen X.-Y, Nie X.-X, Wu Y, Wang P. Chem. Commun. 2020; 56: 5058