Abstract
The formation of C–C bonds from arenes and heteroarenes through transition metal-catalyzed C–H bond functionalizations is one of the major achievements of these last decades. It is now possible to perform such transformations under mild reaction conditions with the help of visible light photocatalysis leading to eco-friendly and safer process to build organic molecules or materials. This chapter will focus on photoredox catalysis which involves a C(sp2)–H bond functionalization step for the formation of C(sp2)–C bonds [i.e., direct arylations and (perfluoro)alkylations] and will show how this hot topic contributes to the development of green chemistry.
The original version of this chapter was revised. The correction to this chapter can be found at DOI 10.1007/3418_2018_25.
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23 January 2019
There was a correction received for Fig. 1 and it was updated in this chapter later.
References
Satoh T, Miura M (2007) Chem Lett 36(2):200–205
Seregin IV, Gevorgyan V (2007) Chem Soc Rev 36(7):1173–1193
Bellina F, Rossi R (2009) Chem Rev 110(2):1082–1146
Chen X, Engle KM, Wang D-H, Yu J-Q (2009) Angew Chem Int Ed 48(28):5094–5115
Colby DA, Bergman RG, Ellman JA (2009) Chem Rev 110(2):624–655
Litvinas ND, Brodsky BH, Du BJ (2009) Angew Chem Int Ed 48(25):4513–4516 S4513/4511-S4513/4512
Cho SH, Kim JY, Kwak J, Chang S (2011) Chem Soc Rev 40(10):5068–5083
Liu C, Zhang H, Shi W, Lei A (2011) Chem Rev 111(3):1780–1824
Yeung CS, Dong VM (2011) Chem Rev 111(3):1215–1292
Arockiam PB, Bruneau C, Dixneuf PH (2012) Chem Rev 112(11):5879–5918
Mercier LG, Leclerc M (2013) Acc Chem Res 46(7):1597–1605
Dixneuf PH, Doucet H (eds) C-H bond activation and catalytic functionalization Vol I (2015) & Vol II (2016) C-H bond activation and catalytic functionalization I. Springer International Publishing, Cham
Bheeter CB, Chen L, Soulé J-F, Doucet H (2016) Cat Sci Technol 6(7):2005–2049
Lyons TW, Sanford MS (2010) Chem Rev 110(2):1147–1169
Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F (2012) Angew Chem Int Ed 51(41):10236–10254
Gafney HD, Adamson AW (1972) J Am Chem Soc 94(23):8238–8239
Balzani V, Juris A (2001) Coord Chem Rev 211(1):97–115
Yoon TP, Ischay MA, Du J (2010) Nat Chem 2:527–532
Tucker JW, Stephenson CRJ (2012) J Org Chem 77(4):1617–1622
Prier CK, Rankic DA, MacMillan DWC (2013) Chem Rev 113(7):5322–5363
Ravelli D, Fagnoni M, Albini A (2013) Chem Soc Rev 42(1):97–113
Angnes RA, Li Z, Correia CRD, Hammond GB (2015) Org Biomol Chem 13(35):9152–9167
Romero NA, Nicewicz DA (2016) Chem Rev 116(17):10075–10166
Douglas JJ, Sevrin MJ, Stephenson CRJ (2016) Org Process Res Dev 20(7):1134–1147
Shaw MH, Twilton J, MacMillan DWC (2016) J Org Chem 81(16):6898–6926
Courant T, Masson G (2016) J Org Chem 81(16):6945–6952
Fabry DC, Rueping M (2016) Acc Chem Res 49(9):1969–1979
Xie J, Jin H, Hashmi ASK (2017) Chem Soc Rev 46(17):5193–5203
Qin Q, Jiang H, Hu Z, Ren D, Yu S (2017) Chem Rec 17(8):754–774
Boubertakh O, Goddard J-P (2017) Eur J Org Chem 2017(15):2072–2084
Cano-Yelo H, Deronzier A (1984) J Chem Soc. Perkin Trans 2(6):1093–1098
Luca OR, Gustafson JL, Maddox SM, Fenwick AQ, Smith DC (2015) Org Chem Front 2(7):823–848
Liu Y-X, Xue D, Wang J-D, Zhao C-J, Zou Q-Z, Wang C, Xiao J (2013) Synlett 24(04):507–513
Tobisu M, Furukawa T, Chatani N (2013) Chem Lett 42(10):1203–1205
Yang F, Koeller J, Ackermann L (2016) Angew Chem Int Ed 55(15):4759–4762
Ghosh I, Shaikh RS, König B (2017) Angew Chem Int Ed 56(29):8544–8549
Natarajan P, Bala A, Mehta SK, Bhasin KK (2016) Tetrahedron 72(19):2521–2526
Yuan K, Soulé J-F, Dorcet V, Doucet H (2016) ACS Catal 8121–8126
Yuan K, Soulé J-F, Doucet H (2015) ACS Catal 5(2):978–991
Hfaiedh A, Yuan K, Ben Ammar H, Ben Hassine B, Soulé J-F, Doucet H (2015) ChemSusChem 8:1794–1804
Skhiri A, Beladhria A, Yuan K, Soulé J-F, Ben Salem R, Doucet H (2015) Eur J Org Chem (20):4428–4436
Hagui W, Besbes N, Srasra E, Roisnel T, Soulé J-F, Doucet H (2016) Org Lett 18(17):4182–4185
Arora A, Weaver JD (2016) Org Lett 18(16):3996–3999
Nagib DA, MacMillan DWC (2011) Nature 480(7376):224–228
Dolbier WR (1997) Fluorinated free radicals. In: Organofluorine chemistry. Springer, Berlin, pp 97–163
Heaton CA, Miller AK, Powell RL (2001) J Fluor Chem 107(1):1–3
Iqbal N, Choi S, Ko E, Cho EJ (2012) Tetrahedron Lett 53(15):2005–2008
Straathof NJW, Gemoets HPL, Wang X, Schouten JC, Hessel V, Noël T (2014) ChemSusChem 7(6):1612–1617
Su Y, Kuijpers KPL, König N, Shang M, Hessel V, Noël T (2016) Chem Eur J 22(35):12295–12300
Lin Q, Chu L, Qing F-L (2013) Chin J Chem 31(7):885–891
Prakash GKS, Hu J (2007) Acc Chem Res 40(10):921–930
Su Y-M, Hou Y, Yin F, Xu Y-M, Li Y, Zheng X, Wang X-S (2014) Org Lett 16(11):2958–2961
Wang L, Wei X-J, Lei W-L, Chen H, Wu L-Z, Liu Q (2014) Chem Commun 50(100):15916–15919
Beatty JW, Douglas JJ, Cole KP, Stephenson CRJ (2015) Nat Commun 6:7919
Beatty Joel W, Douglas James J, Miller R, McAtee Rory C, Cole Kevin P, Stephenson Corey RJ (2016) Chem 1(3):456–472
Tucker JW, Narayanam JMR, Krabbe SW, Stephenson CRJ (2010) Org Lett 12(2):368–371
Furst L, Matsuura BS, Narayanam JMR, Tucker JW, Stephenson CRJ (2010) Org Lett 12(13):3104–3107
Swift EC, Williams TM, Stephenson CRJ (2016) Synlett 27(05):754–758
McCallum T, Barriault L (2016) Chem Sci 7(7):4754–4758
Klauck FJR, James MJ, Glorius F (2017) Angew Chem Int Ed Engl 56(40):12336–12339
Lebée C, Languet M, Allain C, Masson G (2016) Org Lett 18(6):1478–1481
Xue D, Jia Z-H, Zhao C-J, Zhang Y-Y, Wang C, Xiao J (2014) Chem Eur J 20(10):2960–2965
Cano-Yelo H, Deronzier A (1987) J Photochem 37(2):315–321
Zhang J, Chen J, Zhang X, Lei X (2014) J Org Chem 79(21):10682–10688
Candish L, Freitag M, Gensch T, Glorius F (2017) Chem Sci 8(5):3618–3622
DiRocco DA, Dykstra K, Krska S, Vachal P, Conway DV, Tudge M (2014) Angew Chem Int Ed 53(19):4802–4806
Li G-X, Morales-Rivera CA, Wang Y, Gao F, He G, Liu P, Chen G (2016) Chem Sci 7(10):6407–6412
Jin J, MacMillan DWC (2015) Nature 525(7567):87–90
Garza-Sanchez RA, Tlahuext-Aca A, Tavakoli G, Glorius F (2017) ACS Catal 7(6):4057–4061
Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS (2011) J Am Chem Soc 133(46):18566–18569
Liang L, Xie M-S, Wang H-X, Niu H-Y, Qu G-R, Guo H-M (2017) J Org Chem 82(11):5966–5973
Xie J, Yuan X, Abdukader A, Zhu C, Ma J (2014) Org Lett 16(6):1768–1771
Gao G-L, Yang C, Xia W (2017) Chem Commun 53(6):1041–1044
Jung J, Kim E, You Y, Cho EJ (2014) Adv Synth Catal 356(13):2741–2748
Cheng J, Deng X, Wang G, Li Y, Cheng X, Li G (2016) Org Lett 18(18):4538–4541
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Dixneuf, P.H., Soulé, JF. (2018). Functionalization of C(sp2)–H Bonds of Arenes and Heteroarenes Assisted by Photoredox Catalysts for the C–C Bond Formation. In: Dixneuf, P., Soulé, JF. (eds) Organometallics for Green Catalysis. Topics in Organometallic Chemistry, vol 63. Springer, Cham. https://doi.org/10.1007/3418_2018_22
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DOI: https://doi.org/10.1007/3418_2018_22
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