Recent Advances in C–Br Bond Formation

Jonathan Wong; Ying-Yeung Yeung

doi:10.1055/s-0037-1610772

Synlett, Table of Contents

Synlett 2021; 32(13): 1354-1364
DOI: 10.1055/s-0037-1610772

cluster

Perspectives on Heteroatom and Organometallic Chemistry

Recent Advances in C–Br Bond Formation

Jonathan Wong

,

Ying-Yeung Yeung ∗

Abstract

All articles of this category

Abstract

Organobromine compounds are extremely useful in organic synthesis. In this perspective, a focused discussion on some recent advancements in C–Br bond-forming reactions is presented.

1 Introduction

2 Selected Recent Advances

2.1 Catalytic Asymmetric Bromopolycyclization of Olefinic Substrates

2.2 Catalytic Asymmetric Intermolecular Bromination

2.3 Some New Catalysts and Reagents for Bromination

2.4 Catalytic Site-Selective Bromination of Aromatic Compounds

2.5 sp³ C–H Bromination via Atom Transfer/Cross-Coupling

3 Outlook

Key words

bromine - bromination - alkenes - catalysis - halogens

Full Text

References

References
1 Saikia I, Borah AJ, Phukan P. Chem. Rev. 2016; 116: 6837

2a Gelmont M, Yuzefovitch M, Yoffe D, Eden E, Levchik S. Polymers 2020; 12: 352
2b Kaspersma J, Doumen C, Munro S, Prins A.-M. Polym. Degrad. Stab. 2002; 77: 325
2c Covaci A, Harrad S, Abdallah MA.-E, Ali N, Law RJ, Herzke D, de Wit CA. Environ. Int. 2011; 37: 532
2d Zuiderveen EA. R, Slootweg JC, de Boer J. Chemosphere 2020; 255: 126816

3a Vollmer MK, Mühle J, Trudinger CM, Rigby M, Montzka SA, Harth CM, Miller BR, Henne S, Krummel PB, Hall BD, Young D, Kim J, Arduini J, Wenger A, Yao B, Reimann S, O’Doherty S, Maione M, Etheridge DM, Li S, Verdonik DP, Park S, Dutton G, Steele LP, Lunder CR, Rhee TS, Hermansen O, Schmidbauer N, Wang RH. J, Hill M, Salameh PK, Langenfelds RL, Zhou L, Blunier T, Schwander J, Elkins JW, Butler JH, Simmonds PG, Weiss RF, Prinn RG, Fraser PJ. J. Geophys. Res.: Atmos. 2016; 121: 3663
3b Schauffler SM, Atlas EL, Flocke F, Lueb RA, Stroud V, Travnicek W. Geophys. Res. Lett. 1998; 25: 317

4a Kurtz JB, Davis V. Lancet 1988; 331: 304
4b Carpenter JF, Nalepa CJ. In SPE International Symposium on Oilfield Chemistry . Society of Petroleum Engineers; Richardson (TX, USA): 2005
4c Tachikawa M, Tezuka M, Morita M, Isogai K, Okada S. Water Res. 2005; 39: 4126

5a Fromm GH, Terrence CF, Chattha AS. Epilepsia 1983; 24: 394
5b Wheatley AM, Kaduk JA, Gindhart AM, Blanton TN. Powder Diffr. 2018; 33: 298

6 Jeschke P. Pest Manage. Sci. 2010; 66: 10

7a Benkhaya S, M’rabet S, El Harfi A. Inorg. Chem. Commun. 2020; 115: 107891
7b Peng H, Saunders DM. V, Sun J, Jones PD, Wong CK. C, Liu H, Giesy JP. Environ. Sci. Technol. 2016; 50: 12669

8a Gribble GW. J. Chem. Educ. 2004; 81: 1441
8b Gribble GW. Environ. Sci. Pollut. Res. 2000; 7: 37
8c Bidleman TF, Andersson A, Jantunen LM, Kucklick JR, Kylin H, Letcher RJ, Tysklind M, Wong F. Emerging Contaminants 2019; 5: 89
8d Peng H, Chen C, Saunders DM. V, Sun J, Tang S, Codling G, Hecker M, Wiseman S, Jones PD, Li A, Rockne KJ, Giesy JP. Anal. Chem. 2015; 87: 10237
8e Peng H, Chen C, Cantin J, Saunders DM. V, Sun J, Tang S, Codling G, Hecker M, Wiseman S, Jones PD, Li A, Rockne KJ, Sturchio NC, Giesy JP. Environ. Sci. Technol. 2016; 50: 321
8f Peng H, Chen C, Cantin J, Saunders DM. V, Sun J, Tang S, Codling G, Hecker M, Wiseman S, Jones PD, Li A, Rockne KJ, Sturchio NC, Cai M, Giesy JP. Environ. Sci. Technol. 2016; 50: 10097
8g Ueno D, Darling C, Alaee M, Pacepavicius G, Teixeira C, Campbell L, Letcher RJ, Bergman Å, Marsh G, Muir D. Environ. Sci. Technol. 2008; 42: 1657

9 Zhang X, Tan C.-H. Chem 2021; 7: 1
10 In Organic Chemistry, 2nd ed. . Clayden J, Greeves N, Warren S. Oxford University Press; Oxford: 2012: 348
11 Ioffe D, Frim R. In Kirk-Othmer Encyclopedia of Chemical Technology . John Wiley & Sons; Hoboken: 2011
12 Lin R, Amrute AP, Pérez-Ramírez J. Chem. Rev. 2017; 117: 4182

13a Choudhury LH, Parvin T, Khan AT. Tetrahedron 2009; 65: 9513
13b Vekariya RH, Patel HD. Tetrahedron 2014; 70: 3949
13c Cresswell AJ, Eey ST. C, Denmark SE. Angew. Chem. Int. Ed. 2015; 54: 15642
13d Ueda M, Kano T, Maruoka K. Org. Biomol. Chem. 2009; 7: 2005
13e Mustafayeva FA, Kakhramanov NT. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 2019; 62: 47
13f Cantillo D, Kappe CO. React. Chem. Eng. 2017; 2: 7
13g Voskressensky L, Golantsov N, Maharramov A. Synthesis 2016; 48: 615
13h Rajbongshi KK, Borah AJ, Phukan P. Synlett 2016; 27: 1618

14a Sanford MS, Cook A. Science of Synthesis: Catalytic Transformations via C–H Activation 2. Yu J.-Q. Thieme; Stuttgart: 2019
14b Van Pée KH. Methods Enzymol. 2012; 516: 237
14c Larock RC. Comprehensive Organic Transformations . VCH Publishers; New York: 1999: 171-178

15a Neverov AA, Brown RS. J. Org. Chem. 1996; 61: 962
15b Denmark SE, Burk MT, Hoover AJ. J. Am. Chem. Soc. 2010; 132: 1232

16 Denmark SE, Burk MT. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 20655

17a Cai Y, Liu X, Zhou P, Feng X. J. Org. Chem. 2019; 84: 1
17b Kristianslund R, Tungen JE, Hansen TV. Org. Biomol. Chem. 2019; 17: 3079
17c Moore B. Synlett 2018; 29: 401
17d Kawato Y, Hamashima Y. Synlett 2018; 29: 1257
17e Gieuw MH, Ke Z, Yeung Y.-Y. Chem. Rec. 2017; 17: 287
17f Cheng YA, Yu WZ, Yeung YY. Org. Biomol. Chem. 2014; 12: 2333
17g Hennecke U, Wilking M. Synlett 2014; 25: 1633
17h Nolsøe JM. J, Hansen TV. Eur. J. Org. Chem. 2014; 15: 3051
17i Tan CK, Yu WZ, Yeung Y.-Y. Chirality 2014; 26: 328
17j Tripathi CB, Mukherjee S. Synlett 2014; 25: 163
17k Zheng S, Schienebeck CM, Zhang W, Wang HY, Tang W. Asian J. Org. Chem. 2014; 3: 366
17l Fujioka H, Murai K. Heterocycles 2013; 87: 763
17m Mendoza AJ, Fananas F, Rodríguez F. Curr. Org. Synth. 2013; 10: 384
17n Tan CK, Yeung Y.-Y. Chem. Commun. 2013; 49: 7985
17o Denmark SE, Kuester WE, Burk MT. Angew. Chem. Int. Ed. 2012; 51: 10938
17p Hennecke U. Chem. Asian J. 2012; 7: 456
17q Fujioka H. Synlett 2012; 23: 825
17r Tan C, Zhou L, Yeung Y.-Y. Synlett 2011; 1335
17s Chen G, Ma S. Angew. Chem. Int. Ed. 2010; 49: 8306

18 Chung W, Vanderwal CD. Angew. Chem. Int. Ed. 2016; 55: 4396

19a D’Hollander AC. A, Peilleron L, Grayfer TD, Cariou K. Synthesis 2019; 51: 1753
19b Snyder SA, Treitler DS. Angew. Chem. Int. Ed. 2009; 48: 7899

20a Sakakura A, Ukai A, Ishihara K. Nature 2007; 445: 900
20b Sawamura Y, Ogura Y, Nakatsuji H, Sakakura A, Ishihara K. Chem. Commun. 2016; 52: 6068
20c Samanta RC, Yamamoto H. J. Am. Chem. Soc. 2017; 139: 1460
20d Zheng T, Wang X, Ng W.-H, Tse Y.-LS, Yeung Y.-Y. Nat. Catal. 2020; 3: 993

21a Ashtekar KD, Vetticatt M, Yousefi R, Jackson JE, Borhan B. J. Am. Chem. Soc. 2016; 138: 8114
21b Rengevich EN, Shilov EA, Staninet VI. Dokl. Akad. Nauk SSSR 1962; 146: 111
21c Staninets VI, Shilov EA. Russ. Chem. Rev. 1971; 40: 272
21d Williams DL. H, Bienvenüe-Goetz E, Dubois JE. J. Chem. Soc. B 1969; 517
21e Bienvenüe-Goetz E, Dubois JE, Pearson DW, Williams DL. H. J. Chem. Soc. B 1970; 1275
21f Cambie RC, Hayward RC, Roberts JL, Rutledge PS. J. Chem. Soc., Perkin Trans. 1 1974; 1864
21g Doi JT, Luehr GW, Delcarmen D, Lippsmeyer BC. J. Org. Chem. 1989; 54: 2764
21h Snider BB, Johnston MI. Tetrahedron Lett. 1985; 26: 5497

22a Hafez AM, Taggi AE, Wack H, Esterbrook J, Lectka T. Org. Lett. 2001; 3: 2049
22b Bartoli G, Bosco M, Carlone A, Locatelli M, Melchiorre P, Sambri L. Angew. Chem. 2005; 117: 6375
22c Jiang H, Elsner P, Jensen KL, Falcicchio A, Marcos V, Jørgensen KA. Angew. Chem. Int. Ed. 2009; 48: 6844
22d Kano T, Shirozu F, Maruoka K. Chem. Commun. 2010; 46: 7590

23a Chen Z.-M, Zhang Q.-W, Chen Z.-H, Li H, Tu Y.-Q, Zhang F.-M, Tian J.-M. J. Am. Chem. Soc. 2011; 133: 8818
23b Li H, Zhang F.-M, Tu Y.-Q, Zhang Q.-W, Chen Z.-M, Chen Z.-H, Li J. Chem. Sci. 2011; 2: 1839
23c Wang S.-H, Li B.-S, Tu Y.-Q. Chem. Commun. 2014; 50: 2393
23d Song Z.-L, Fan C.-A, Tu Y.-Q. Chem. Rev. 2011; 111: 7523
23e Wang B, Tu YQ. Acc. Chem. Res. 2011; 44: 1207
23f Müller CH, Wilking M, Rühlmann A, Wibbeling B, Hennecke U. Synlett 2011; 2043

24a Chen J, Zhou L. Synthesis 2014; 46: 586
24b Cresswell AJ, Eey ST.-C, Denmark SE. Angew. Chem. Int. Ed. 2015; 54: 15642
24c Bock J, Guria S, Wedek V, Hennecke U. Chem. Eur. J. 2021; 27: 4517

25 Tang LiG, Fu Q, Zhang X, Jiang J, Tang Z. Tetrahedron: Asymmetry 2012; 23: 245

26a Zhang X, Li J, Tian H, Shi Y. Chem. Eur. J. 2015; 21: 11658
26b Li L, Su C, Liu X, Tian H, Shi Y. Org. Lett. 2014; 16: 3728
26c Li J, Li Z, Zhang X, Xu B, Shi Y. Org. Chem. Front. 2017; 4: 1084
26d Alix A, Lalli C, Retailleau P, Masson G. J. Am. Chem. Soc. 2012; 134: 10389

27a Zhang W, Liu N, Schienebeck CM, Zhou X, Izhar II, Guzeiband IA, Tang W. Chem. Sci. 2013; 4: 2652
27b Soltanzadeh B, Jaganathan A, Staples RJ, Borhan B. Angew. Chem. Int. Ed. 2015; 54: 9517
27c Soltanzadeh B, Jaganathan A, Yi Y, Yi H, Staples RJ, Borhan B. J. Am. Chem. Soc. 2017; 139: 2132
27d Qi J, Fan G.-T, Chen J, Sun M.-H, Dong Y.-T, Zhou L. Chem. Commun. 2014; 50: 13841
27e Cao Y.-M, Lentz D, Christmann M. J. Am. Chem. Soc. 2018; 140: 10677

28a Hu DX, Shibuya GM, Burns NZ. J. Am. Chem. Soc. 2013; 135: 12960
28b Hu DX, Seidl FJ, Bucher C, Burns NZ. J. Am. Chem. Soc. 2015; 137: 3795
28c Seidl FJ, Min C, Lopez JA, Burns NZ. J. Am. Chem. Soc. 2018; 140: 15646

29 Landry ML, Burns NZ. Acc. Chem. Res. 2018; 51: 1260

30a Li W, Zhou P, Li G, Lin L, Feng X. Adv. Synth. Catal. 2020; 362: 1982
30b Zhou P, Cai Y, Zhong X, Luo W, Kang T, Li J, Liu X, Lin L, Feng X. ACS Catal. 2016; 6: 7778
30c Cai Y, Liu X, Hui Y, Jiang J, Wang W, Chen W, Lin L, Feng X. Angew. Chem. Int. Ed. 2010; 49: 6160
30d Cai Y, Liu X, Jiang J, Chen W, Lin L, Feng X. J. Am. Chem. Soc. 2011; 133: 5636
30e Cai YF, Liu XH, Zhou PF, Kuang YL, Lin LL, Feng X. Chem. Commun. 2013; 49: 8054
30f Zhou PF, Lin LL, Chen L, Zhong X, Liu XH, Feng X. J. Am. Chem. Soc. 2017; 139: 13414

31a Olah GA, Bollinger JM. J. Am. Chem. Soc. 1967; 89: 4744
31b Olah GA, Bollinger JM, Brinich J. J. Am. Chem. Soc. 1968; 90: 2587
31c Olah GA, Schilling P, Westermann PW, Lin HC. J. Am. Chem. Soc. 1974; 96: 3581
31d Strating J, Wieringa JH, Wynberg H. Chem. Commun. 1969; 907
31e Slebocka-Tilk H, Ball RG, Brown RS. J. Am. Chem. Soc. 1985; 107: 4504

32a Ascheberg C, Bock J, Buß F, Meck-Lichtenfeld C, Daniliuc CG, Bergander K, Dielmann F, Hennecke U. Chem. Eur. J. 2017; 23: 11578
32b Bock J, Daniliuc CG, Hennecke U. Org. Lett. 2019; 21: 1704

33 Einaru S, Shitamichi K, Nagano T, Matsumoto A, Asano K, Matsubara S. Angew. Chem. Int. Ed. 2018; 57: 13863

34a Braddock DC, Cansell G, Hermitage SA, White AJ. P. Chem. Commun. 2006; 42: 1442
34b Braddock DC, Cansell G, Hermitage SA. Chem. Commun. 2006; 42: 2483
34c Stodulski M, Goetzinger A, Kohlhepp SV, Gulder T. Chem. Commun. 2014; 50: 3435
34d Ulmer A, Stodulski M, Kohlhepp SV, Patzelt C, Pöthig A, Bettray W, Gulder T. Chem. Eur. J. 2015; 21: 1444

35 Arnold A, Pöthig A, Drees M, Gulder T. J. Am. Chem. Soc. 2018; 140: 4344
36 Moriyama K, Kuramochi M, Tsuzuki S, Fujii K, Morita T. Org. Lett. 2021; 23: 268

37a Chen T, Foo TJ. Y, Yeung Y.-Y. ACS Catal. 2015; 5: 4751
37b Shi Y, Ke Z, Yeung Y.-Y. Green. Chem. 2018; 20: 4448

38a Ng W.-H, Hu R.-B, Lam Y.-P, Yeung Y.-Y. Org. Lett. 2020; 22: 5572
38b Ng W.-H, Lam Y.-P, Hu R.-B, Ng W.-L, Yeung Y.-Y. Asian J. Org. Chem. 2021; 10: in press

39a Wang Y.-M, Wu J, Hoong C, Rauniyar V, Toste FD. J. Am. Chem. Soc. 2012; 134: 12928
39b Miller E, Kim S, Gibson K, Derrick JS, Toste FD. J. Am. Chem. Soc. 2020; 142: 8946

40a Taylor CA, Snyder SA. Org. Synth. 2020; 97: 339
40b Snyder SA, Treitler DS. Angew. Chem. Int. Ed. 2009; 48: 7899
40c Taylor CA, Zhang Y, Snyder SA. Chem. Sci. 2020; 11: 3036
40d Schevenels F, Shen M, Snyder SA. J. Am. Chem. Soc. 2017; 139: 6329

41a Dubost E, Fossey C, Cailly T, Rault S, Fabis F. J. Org. Chem. 2011; 76: 6414
41b Schröder N, Wencel-Delord J, Glorius F. J. Am. Chem. Soc. 2012; 134: 8298
41c John A, Nicholas KM. J. Org. Chem. 2012; 77: 5600
41d Bhattarai BT, Adhikari S, Kimball EA, Moore JN, Shaughnessy KH, Snowden TS, Fronczek FR, Dolliver DD. Tetrahedron Lett. 2014; 55: 4801
41e Zhang P, Hong L, Li G, Wang R. Adv. Synth. Catal. 2015; 357: 345
41f Cheng Y, Dong W, Parthasarathy K, Bolm C. Org. Lett. 2017; 19: 726
41g Jaiswal Y, Kumar Y, Kumar A. Org. Biomol. Chem. 2019; 17: 6809
41h Tanaka J, Shibata Y, Joseph A, Nogami J, Terasawa J, Yoshimura R, Tanaka K. Chem. Eur. J. 2020; 26: 5774
41i Arnold PL, Sanford MS, Pearson SM. J. Am. Chem. Soc. 2009; 131: 13912

CH activation ortho bromination:

41j Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
41k Albrecht M. Chem. Rev. 2010; 110: 576
41l Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
41m Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
41n Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936

42 Teskey CJ, Lui AY. W, Greaney MF. Angew. Chem. Int. Ed. 2015; 54: 11677
43 Yu Q, Hu L, Wang Y, Zheng S, Huang J. Angew. Chem. Int. Ed. 2015; 54: 15284
44 Mori K, Ichikawa Y, Kobayashi M, Shibata Y, Yamanaka M, Akiyama T. J. Am. Chem. Soc. 2013; 135: 3964

45a Metrano AJ, Miller SJ. Acc. Chem. Res. 2019; 52: 199
45b Gustafson JL, Lim D, Miller SJ. Science 2010; 328: 1251
45c Diener ME, Metrano AJ, Kusano S, Miller SJ. J. Am. Chem. Soc. 2015; 137: 12369
45d Barrett KT, Metrano AJ, Rablen PR, Miller SJ. Nature 2014; 509: 71

46 Miyaji R, Asano K, Matsubara S. J. Am. Chem. Soc. 2015; 137: 6766
47 Vaidya SD, Toenjes ST, Yamamoto N, Maddox SM, Gustafson JL. J. Am. Chem. Soc. 2020; 142: 2198
48 Xiong X, Zheng T, Wang X, Tse Y.-LS, Yeung Y.-Y. Chem 2020; 6: 919
49 Tu H, Zhu S, Qing F.-L, Chu L. Tetrahedron Lett. 2018; 59: 173
50 Kee CW, Chan KM, Wong MW, Tan C.-H. Asian J. Org. Chem. 2014; 3: 536
51 Schmidt VA, Quinn RK, Brusoe AT, Alexanian EJ. J. Am. Chem. Soc. 2014; 136: 14389
52 Wang Y, Li G.-X, Yang G, He G, Chen G. Chem. Sci. 2016; 7: 2679

53a Clark AJ. Eur. J. Org. Chem. 2016; 2231
53b Gao Y, Zhang P, Ji Z, Tang G, Zhao Y. ACS Catal. 2017; 7: 186

54a Gao Y, Zhang P, Ji Z, Tang G, Zhao Y. ACS Catal. 2017; 7: 186
54b Van Hoveln RJ, Schmid SC, Tretbar M, Buttke CT, Schomaker JM. Chem. Sci. 2014; 5: 4763

55 Clark AJ, Battle GM, Bridge A. Tetrahedron Lett. 2001; 42: 1999
56 Sathyamoorthi S, Banerjee S, Du Bois J, Burns NZ, Zare RN. Chem. Sci. 2018; 9: 100
57 Rit RK, Yadav MR, Ghosh K, Shankar M, Sahoo AK. Org. Lett. 2014; 16: 5258
58 Zhu R.-Y, Saint-Denis TG, Shao Y, He J, Sieber JD, Senanayake CH, Yu J.-Q. J. Am. Chem. Soc. 2017; 139: 5724
59 Wedek V, Van Lommel R, Daniliuc CG, De Proft F, Hennecke U. Angew. Chem. Int. Ed. 2019; 58: 9239

60a Rosner C, Hennecke U. Org. Lett. 2015; 17: 3226
60b Gieuw MH, Chen S, Ke Z, Houk KN, Yeung Y.-Y. Chem. Sci. 2020; 11: 9426
60c Wong Y.-C, Ke Z, Yeung Y.-Y. Org. Lett. 2015; 17: 4944

61a Mao H, Tang Z, Hu H, Cheng Y, Zheng W.-H, Zhu C. Chem. Commun. 2014; 50: 9773
61b Ma C, Xing D, Hu W. Org. Lett. 2016; 18: 3134
61c Wang X, Dong K, Yan B, Zhang C, Qiu L, Xu X. RSC Adv. 2016; 6: 70221

62a Tan Z, Liu Y, Helmy R, Rivera NR, Hesk D, Tyagarajan S, Yang L, Su J. Tetrahedron Lett. 2017; 58: 3014
62b Yu K, Kong X, Yang J, Li G, Xu B, Chen Q. J. Org. Chem. 2021; 86: 917
62c Yang X, Yang Q.-L, Wang X.-Y, Xu H.-H, Mei T.-S, Huang Y, Fang P. J. Org. Chem. 2020; 85: 3497
62d Sun X, Ma H.-X, Mei T.-S, Fang P, Hu Y. Org. Lett. 2019; 21: 3167
62e Jagatheesan R, Joseph Santhana Raj K, Lawrence S, Christopher C. RSC Adv. 2016; 6: 35602
62f Xu J, Tong R. Green Chem. 2017; 19: 2952
62g Yuan Y, Yao A, Zheng Y, Gao M, Zhou Z, Qiao J, Hu J, Ye B, Zhao J, Wen H, Lei A. iScience 2019; 12: 293
62h Xie W, Ning S, Liu N, Bai Y, Wang S, Wang S, Shi L, Che X, Xiang J. Synlett 2019; 30: 1313

63a Ochiai M, Miyamoto K, Kaneaki T, Hayashi S, Nakanishi W. Science 2011; 332: 448
63b Ochiai M, Nishi Y, Goto S, Shiro M, Frohn HJ. J. Am. Chem. Soc. 2003; 125: 15304
63c Ochiai M, Kaneaki T, Tada N, Miyamoto K, Chuman H, Shiro M, Hayashi S, Nakanishi W. J. Am. Chem. Soc. 2007; 129: 12938
63d Ochiai M, Yoshimura A, Miyamoto K, Hayashi S, Nakanishi W. J. Am. Chem. Soc. 2010; 132: 9236
63e Farooq U, Ali Shah A, Wirth T. Angew. Chem. Int. Ed. 2009; 48: 1018
63f Miyamoto K. Chemistry of Hypervalent Bromine. In PATAI’S Chemistry of Functional Groups. John Wiley & Sons; Hoboken: 2018

64a Xu J, Liang L, Zheng H, Chi YR, Tong R. Nat. Commun. 2019; 10: 4754
64b Lu Y, Nakatsuji H, Okumura Y, Yao L, Ishihara K. J. Am. Chem. Soc. 2018; 140: 6039
64c Uyanik M, Fukatsu R, Ishihara K. Chem. Asian J. 2010; 5: 456
64d Wang H, Wang Z, Wang Y.-L, Zhou R.-R, Wu G.-C, Yin S.-Y, Yan X, Wang B. Org. Lett. 2017; 19: 6140
64e Grabowski SJ. Chem. Phys. Lett. 2014; 605: 131
64f Cavallo G, Metrangolo P, Milani R, Pilati T, Priimagi A, Resnati G, Terraneo G. Chem. Rev. 2016; 116: 2478