Photocatalytic Homocoupling Transformations

María de Gracia Retamosa; Haci Ali Döndaş; Sara Sobhani; Carmen Nájera; Miguel A. Yus; José M. Sansano

doi:10.1055/a-1517-7329

Synthesis, Table of Contents

Synthesis 2021; 53(20): 3653-3672
DOI: 10.1055/a-1517-7329

review

Photocatalytic Homocoupling Transformations

María de Gracia Retamosa

^aDepartamento de Química Orgánica e Instituto de Síntesis Orgánica, Universidad de Alicante, 03080-Alicante, Spain

^bCentro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, 03080-Alicante, Spain

,

Haci Ali Döndaş

^cDepartment of Basic Pharmaceutical Sciences, Faculty of Pharmacy, Çukurova University, 01330, Adana, Turkey

,

Sara Sobhani

^dDepartment of Chemistry, College of Sciences, University of Birjand, Birjand, Iran

,

Carmen Nájera

^bCentro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, 03080-Alicante, Spain

,

Miguel A. Yus

^bCentro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, 03080-Alicante, Spain

,

José M. Sansano ∗

^aDepartamento de Química Orgánica e Instituto de Síntesis Orgánica, Universidad de Alicante, 03080-Alicante, Spain

^bCentro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, 03080-Alicante, Spain

› Author Affiliations

Abstract

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Dedicated to the memory of Prof. Pedro Molina

Abstract

Homocoupling reactions promoted by photocatalysts are not very abundant in the literature. However, the products generated from such processes are very interesting. In this review, we highlight the most relevant reports concerning photocatalyzed dimerizations covering the literature until the middle of 2020. Reactions will be classified according to the type of starting material employed, with an emphasis being placed on the corresponding mechanism.

1 Introduction

2 Arenes and Heteroarenes

3 Alkenes

4 Alkanes

5 Alkynes

6 Aldehydes, Ketones, Alcohols, Amines and Imines

7 Carboxylic Acids

8 Nitro Compounds

9 Conclusions

Key words

photocatalysis - photoredox - sensitizers - homocoupling - dimerization

Full Text

References

References

1a Shaw MH, Twilton J, MacMillan DW. C. J. Org. Chem. 2016; 81: 6898
1b Ravelli D, Protti S, Fagnoni M. Chem. Rev. 2016; 116: 9850

For recent reviews, see:

2a Gopalan-Sibi M, Verma D, Kim J. Cat. Rev. Sci. Eng. 2020; 62: 163
2b Haug WK, Moscarello EM, Wolfson ER, McGrier PL. Chem. Soc. Rev. 2020; 49: 839
2c Prentice C, Morrisson J, Smith AD, Zysman-Colman E. Beilstein J. Org. Chem. 2020; 16: 2363

For recent reviews, see:

3a Markushyna Y, Smith CA, Savateev A. Eur. J. Org. Chem. 2020; 1294
3b Zhang T, Xing G, Chen W, Chen L. Mater. Chem. Front. 2020; 4: 332
3c Wang H, Wang H, Wang Z, Tang L, Zeng G, Xu P, Chen M, Xiong T, Zhou C, Li X, Huang D, Zhu Y, Wang Z, Tang J. Chem. Soc. Rev. 2020; 49: 4135
3d Cervantes-González J, Vosburg DA, Mora-Rodríguez SE, Vázquez MA, Zepeda LG, Villegas-Gómez C, Lagunas-Rivera S. ChemCatChem 2020; 12: 3811

For recent reviews, see:

4a De Abreu M, Belmont P, Brachet E. Eur. J. Org. Chem. 2020; 1327
4b Crisenza GE. M, Melchiorre P. Nat. Commun. 2020; 11: 803
4c Garrido-Castro AF, Maestro MC, Alemán J. Catalysts 2020; 10: 562
4d Zhu D.-L, Young DJ, Li H.-X. Synthesis 2020; 52: 3493

For recent reviews, see:

5a Yu X.-Y, Zhao Q.-Q, Chen J, Xiao W.-J, Chen J.-R. Acc. Chem. Res. 2020; 53: 1066
5b Hockin BM, Li C, Robertson N, Zysman-Colman E. Cat. Sci. Tech. 2019; 9: 889

6 Nijamudheen A, Datta A. Chem. Eur. J. 2020; 26: 1442

7a Stanley PA, Spiteri C, Moore JC, Barrow AS, Sharma P, Moses JE. Curr. Pharm. Des. 2016; 22: 1628
7b Wezeman T, Masters K.-S, Braese S. Angew. Chem. Int. Ed. 2014; 53: 4524

8 Ueda H. Chem. Pharm. Bull. 2020; 68: 117
9 Menezes JC. J. M. D. S, Diederich MF. Eur. J. Med. Chem. 2019; 182: 111637

10a Ma L.-F, Chen Y.-L, Shan W.-G, Zhan Z.-J. Nat. Prod. Rep. 2020; 37: 999
10b Zhao W.-Y, Yan J.-J, Liu T.-T, Gao J, Huang H.-L, Sun C.-P, Huo X.-K, Deng S, Zhang B.-J, Ma X.-C. Eur. J. Med. Chem. 2020; 203: 112622
10c Harmange-Magnani CS, Thach DQ, Haelsig KT, Maimone TJ. Acc. Chem. Res. 2020; 53: 949
10d Chen J, Liu B. Synlett 2018; 29: 863

11 Gomes NG. M, Pereira RB, Andrade PB, Valentao P. Marine Drugs 2019; 17: 551
12 Kamo S, Kuramochi K, Tsubaki K. Tetrahedron Lett. 2018; 59: 224
13 Jeon S, Park J, Han S. Synlett 2017; 28: 2353
14 Tykwinski RR. Acc. Chem. Res. 2019; 52: 2056
15 Wang Z, Hou R, Loh IY. Nanoscale 2019; 11: 9240
16 Lee CG, Park JY, Park YI, Jung S.-H, Sung LG, Park JM, Hwang D.-N, Kong H. J. Nanosci. Nanotechnol. 2019; 19: 4782
17 Xiao L, Chen S, Chen X, Peng X, Cao Y, Zhu X. J. Mater. Chem. C 2018; 6: 3341
18 Xiao Q, Li Y, Wu F, Han M, Xie M, Li Z, Zhu L, Li Z. J. Mater. Chem. C 2018; 6: 10547
19 Brycki BE, Kowalczyk IH, Szulc AM, Brycka JA. Tenside Surf. Det. 2018; 55: 432

20a Sarmales-Murga C, Akaoka F, Sato M, Takanishi J, Mino T, Miyoshi N, Watanabe K. J. Antibiot. 2020; 73: 320
20b Liu F, Tian H.-Y, Huang X.-L, Wang W.-J, Li N.-P, He J, Ye W.-C, Wang L. J. Org. Chem. 2019; 84: 15355
20c van Harten RM, Willems RJ. L, Martin NI, Hendrickx AP. A. Trends Microbiol. 2017; 25: 467

21 He X, Wang Y, Luo R.-H, Yang L.-M, Wang L, Guo D, Yang J, Deng Y, Zheng Y.-T, Huang S.-X. J. Nat. Prod. 2019; 82: 1813
22 Feizpour F, Jafarpour M, Rezaeifard A. Catal. Lett. 2019; 149: 1595
23 Guo J, Xu Y.-W, Li K, Xiao L.-M, Chen S, Wu K, Chen X.-D, Fan Y.-Z, Liu JM, Su C.-Y. Angew. Chem. Int. Ed. 2017; 56: 3852
24 Tran H, McCallum T, Morin M, Barriault L. Org. Lett. 2016; 18: 4308
25 Masuda Y, Ishida N, Murakami M. Eur. J. Org. Chem. 2016; 5822
26 Kunkely H, Vogler A. Inorg. Chim. Acta 2000; 300–302: 1090
27 Liu C, Fei Y.-y, Zhang H.-l, Pan C.-y, Hong C.-y. Macromolecules 2019; 52: 176

28a Hayashi T, Maeda K. Bull. Chem. Soc. Jpn. 1960; 33: 565
28b Hayashi T, Maeda K. Bull. Chem. Soc. Jpn. 1962; 35: 2057

29 Al-Dies A.-AM, Asiri AM, Osman OI, Khan SA. Res. J. Appl. Sci. 2018; 13: 616

30a Kishimoto Y, Abe J. J. Am. Chem. Soc. 2009; 131: 4227
30b Shima K, Mutoh K, Kobayashi Y, Abe J. J. Am. Chem. Soc. 2014; 136: 3796

31 Iwasaki T, Kato T, Kobayashi Y, Abe J. Chem. Commun. 2014; 50: 7481

32a Hatano S, Horino T, Tokita A, Oshima T, Abe J. J. Am. Chem. Soc. 2013; 135: 3164
32b Yamaguchi T, Hatano S, Abe J. J. Phys. Chem. A 2014; 118: 134

33 Yamamoto K, Mutoh K, Abe J. J. Phys. Chem. A 2019; 123: 1945
34 Mutoh K, Arai H, Kobayashi Y, Abe J. Pure Appl. Chem. 2015; 87: 511
35 Sarkar D, Bera N, Ghosh S. Eur. J. Org. Chem. 2020; 1310 ; and references cited therein
36 Selig P, Bach T. J. Org. Chem. 2006; 71: 5662
37 For an interesting cyclobutene core in a natural product, see: Ma Z, Wang X, Wang X, Rodríguez RA, Moore CE, Gao S, Tan X, Ma Y, Rheingold AL, Baran PS, Chen C. Science 2014; 346: 219

For general recent [2+2] reactions in the search for new applications, novel materials and as result of secondary products, see:

38a Sima J.-Y, Li H.-X, Young DJ, Braunstein P, Lang J.-P. Chem. Commun. 2019; 55: 3532
38b Rath BB, Kole GK, Morris SA, Vittal JJ. Chem. Commun. 2020; 56: 6289
38c Peng J, Ye K, Liu C, Sun J, Lu R. J. Mater. Chem. C 2019; 7: 5433
38d Giménez RE, Serrano MP, Álvarez R, María S, Martino DM, Borsarelli CD. ChemPlusChem 2019; 84: 504
38e Zhao L.-M, Lei T, Liao R.-Z, Xiao H, Chen B, Ramamurthy V, Tung C.-H, Wu L.-Z. J. Org. Chem. 2019; 84: 9257
38f Zelenak V, Benova E, Almasi M, Halamova D, Hornebecq V, Hronsky V. New J. Chem. 2018; 42: 13263
38g Zhou C, Lei T, Wei X.-Z, Liu Z, Chen B, Ramamurthy V, Tung C.-H, Wu L.-Z. Org. Lett. 2018; 20: 6808
38h Rath BB, Kole GK, Vittal JJ. Cryst. Growth Design 2018; 18: 6221
38i Quah HS, Yap J, Li X, Sambasivam U, Chanthapally A, Donnadieu B, Vittal JJ. Cryst. Growth Design 2018; 18: 3693
38j Voevodin A, Campos LM, Roy X. J. Am. Chem. Soc. 2018; 140: 5607
38k Garai M, Biradha K. Chem. Eur. J. 2017; 23: 273
38l Gong L.-L, Feng XF, Luo F, Yi XF, Zheng AM. Green Chem. 2016; 18: 2047
38m Udagawa A, Johnston P, Sakon A, Toyoshima R, Uekusa H, Koshima H, Saito K, Asahi T. RSC Adv. 2016; 6: 107317
38n Kim JH, Bae JM, Lee HG, Kim NJ, Jung K.-D, Kim C, Kim S.-J, Kim Y. Inorg. Chem. Commun. 2012; 22: 1

39 Wu Q.-A, Chen F, Ren C.-C, Liu X.-F, Chen H, Xu L.-X, Yu X.-C, Luo S.-P. Org. Biomol. Chem. 2020; 18: 3707
40 Fedorova OA, Saifutiarova AE, Gulakova EN, Guskova EO, Aliyeu TM, Shepel NE, Fedorov YV. Photochem. Photobiol. Sci. 2019; 18: 2208
41 Neena KK, Sudhakar P, Thilagar P. Angew. Chem. Int. Ed. 2018; 57: 16806
42 Lei T, Zhou C, Wei XZ, Yang B, Chen B, Tung C.-H, Wu L.-Z. Chem. Eur. J. 2019; 25: 879

43a Ischay MA, Anzovino ME, Du J, Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
43b Tyson EL, Farney EP, Yoon TP. Org. Lett. 2012; 14: 1110

44 Zhao G, Yang C, Guo L, Sun H, Lin R, Xia W. J. Org. Chem. 2012; 77: 6302
45 Wei D, Li Y, Liang F. Adv. Synth. Catal. 2016; 358: 3887
46 Chuskit D, Chaudhary R, Venugopalan P, König B, Natarajan P. Org. Chem. Front. 2018; 5: 3553
47 Zhou M, Wang F, Zhang XH, Tu H.-Y, Zhang XG. J. Fluorine Chem. 2018; 215: 10
48 Das S, Lai D, Mallick A, Roy S. ChemistrySelect 2016; 4: 691
49 McTiernan CD, Morin M, McCallum T, Scaiano JC, Barriault L. Catal. Sci. Technol. 2016; 6: 201
50 Levin VV, Agababyan DP, Struchkova MI, Dilman AD. Synthesis 2018; 50: 2930
51 Fukuzumi S, Ishikawa K, Tanaka T. Organometallics 1987; 6: 358
52 Kerzig C, Wenger OS. Chem. Sci. 2019; 10: 11023
53 Zhang Y, Tia S, Lee TS, Petersen JL, Milsmann C. J. Am. Chem. Soc. 2018; 140: 5934
54 Zhang Y, Petersen JL, Milsmann C. Organometallics 2018; 37: 4488
55 Shukla D, de Rege F, Wan P, Johnston LJ. J. Phys. Chem. 1992; 95: 10240

56a Fang C.-L, Horne S, Taylor N, Rodrigo R. J. Am. Chem. Soc. 1994; 116: 9480
56b Ghosh S, Chaudhuri S, Bisai A. Org. Lett. 2015; 17: 1373

57 Jia W.-L, He J, Yang J.-J, Gao X.-W, Liu Q, Wu L.-Z. J. Org. Chem. 2016; 81: 7172
58 Moreno-Cabrerizo C, Ortega-Martínez A, Esteruelas MA, López AM, Nájera C, Sansano JM. Eur. J. Org. Chem. 2020; 3101
59 Wei D, Liang F. Org. Lett. 2016; 18: 5860
60 Kapuge TK, Thalgaspitiya WR. K, Rathnayake D, He J, Kerns P, Suib SL. App. Catal. B: Environ. 2020; 268: 118386
61 Wang JL, Wang C, de Krafft KE, Lin W. ACS Catal. 2012; 2: 417
62 Dadwal S, Deol H, Kumar M, Bhalla V. Sci. Rep. 2019; 9: 11142
63 Mitkina T, Stanglmair C, Setzer W, Gruber M, Kisch H, König B. Org. Biomol. Chem. 2012; 10: 3556

64a Zeug N, Bücheler J, Kisch H. J. Am. Chem. Soc. 1985; 107: 1459
64b Hetterich W, Kisch H. Chem. Ber. 1987; 121: 15

65 A dehydrogenative C–C coupling using a Ru-doped ZnIn₂S₄ catalyst was employed in dimerizations applied for the production of biodiesel, see: Luo N, Montini T, Zhang J, Fornasiero P, Fonda E, Hou T, Nie W, Lu J, Liu J, Heggen M, Lin L, Ma C, Wang M, Fan F, Jin S, Wang F. Nat. Energy 2019; 4: 575
66 Ciamician G, Silber P. Ber. Dtsch. Chem. Ges. 1900; 33: 2911

67a Terra BS, Macedo FJr. ARKIVOC 2012; (i): : 134
67b Chatterjee A, Joshi NN. Tetrahedron 2006; 62: 12137

68 Xia Q, Dong J, Song H, Wang Q. Chem. Eur. J. 2019; 25: 2949
69 Cao B, Wang X, Chang L, Liu X, Wang H, Guo J, Zhou C. New J. Chem. 2020; 44: 12613
70 Yang C, Wang B, Zhang L, Yin L, Wang X. Angew. Chem. Int. Ed. 2017; 56: 6627
71 Liu M, Tan L, Rashid RT, Cen Y, Cheng S, Botton G, Mi Z, Li C.-J. Chem. Sci. 2020; 11: 7864
72 Li Y, Zhang ZP, Mo WJ, Rong MZ, Zhang MQ, Liu D. Polymer 2020; 192: 122299
73 Qiu Z, Pham HD. M, Li J, Li C.-C, Castillo-Pazos DJ, Khaliullin RZ, Li CJ. Chem. Sci. 2019; 10: 10937
74 Li N, Yan W, Zhang H, Jia S, Wang Z, Zheng J, Zhu Z. New J. Chem. 2017; 41: 2764
75 Pickett JE. J. Polym. Sci., Part A: Polym. Chem. 2017; 55: 2318
76 Das P, Elder T, Brennessel WW, Chmely SC. RSC Adv. 2016; 6: 88050
77 Ma N, Shi W, Zhang R, Zhu Z, Jiang Z. Tetrahedron Lett. 2011; 52: 718
78 Singh R, Garg PK, Hundal MS, Ishar MP. S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2006; 45: 506

79a Gualandi A, Nenov A, Marchini M, Rodeghiero G, Conti I, Paltanin E, Balletti M, Ceroni P, Garavelli M, Cozzi PG. ChemCatChem 2021; 13: 981
79b Gualandi A, Rodeghiero G, Della Rocca E, Bertoni F, Marchini M, Perciaccante R, Jansen TP, Ceroni P, Cozzi PG. Chem. Commun. 2018; 54: 10044

80 Noto N, Hyodo Y, Yoshizawa M, Koike T, Akita M. ACS Catal. 2020; 10: 14283
81 Naumann R, Goez M. Green Chem. 2019; 21: 4470
82 Steiner A, Williams JD, Rincon JA, de Frutos O, Mateos C, Kappe O. Eur. J. Org. Chem. 2019; 5807
83 Nakajima M, Fava E, Loescher S, Jiang Z, Rueping M. Angew. Chem. Int. Ed. 2015; 54: 8828
84 Griesbeck AG, Reckenthäler M. Beilstein J. Org. Chem. 2014; 10: 1143

85a Zhang M, Rouch WD, McCulla RD. Eur. J. Org. Chem. 2012; 6187
85b Rouch WD, Zhang M, McCulla RD. Tetrahedron Lett. 2012; 53: 4942

86 Caron A, Morin E, Collins SK. ACS Catal. 2019; 9: 9458
87 Okamoto S, Kojiyama K, Tsujioka H, Sudo A. Chem. Commun. 2016; 52: 11339
88 Monos TM, Magallanes G, Sebren LJ, Stephenson CR. J. J. Photochem. Photobiol., A 2016; 328: 240
89 Rong J, Seeberger PH, Gilmore K. Org. Lett. 2018; 20: 4081
90 Zhu J, Yuan Y, Wang S, Yao Z.-J. ACS Omega 2017; 2: 4665
91 Gentry EC, Knowles RR. Acc. Chem. Res. 2016; 49: 1546
92 Wang C.-M, Xia P.-J, Xiao J.-A, Li J, Xiang H.-Y, Chen X.-Q, Yang H. J. Org. Chem. 2017; 82: 3895
93 Koike T, Yasu Y, Akita M. Chem. Lett. 2012; 41: 999
94 Shang Z.-P, Zha G.-F, Chen X.-Q, Qin H.-L. Tetrahedron Lett. 2016; 57: 4680
95 Manley DW, Walton JC. Org. Lett. 2014; 16: 5394
96 Gan XY, Keller EL, Warkentin CL, Crawford SE, Frontiera RR, Millstone JL. Nano Lett. 2019; 19: 2384