Reusable Visible Light Photoredox Catalysts; Catalyzed Benzylic C(sp3)–H Functionalization/Carbocyclization Reactions

Jia-Dong Xia; Guo-Bo Deng; Ming-Bo Zhou; Wei Liu; Peng Xie; Jin-Heng Li

doi:10.1055/s-0032-1317349

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(18): 2707-2713
DOI: 10.1055/s-0032-1317349

letter

Reusable Visible Light Photoredox Catalysts; Catalyzed Benzylic C(sp³)–H Functionalization/Carbocyclization Reactions

Jia-Dong Xia

^aState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China

^bKey Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China Fax: +86(731)88713642 eMail: jhli@hnu.edu.cn

,

Guo-Bo Deng

^aState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China

,

Ming-Bo Zhou

^aState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China

,

Wei Liu

^aState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China

,

Peng Xie

^aState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China

^bKey Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China Fax: +86(731)88713642 eMail: jhli@hnu.edu.cn

,

Jin-Heng Li*

^aState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

The C(sp³)–H functionalization/carbocyclization reaction through the oxidative quenching of visible light photoredox catalysts is established for constructing functionalized 1H-indenes. The process is general for a wide range of benzylic C(sp³)–H bonds and is highly compatible with common functional groups. Importantly, the visible light photoredox catalysts can be recovered and reused at least three times without loss of catalytic activity.

Key words

photoredox - catalysis - C–H activation - cyclization - alkynes - indenes

Volltext

Referenzen

References

For reviews, see:

1a Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785
1b Yoon TP, Ischay MA, Du J. Nature Chem. 2010; 2: 527
1c Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
1d Teplý F. Collect. Czech. Chem. Commun. 2011; 76: 859
1e Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617

For papers on C(sp³)–H functionalization using visible-light photoredox catalysis via a reductive quenching cycle, see:

2a Condie AG, González-Gómez J, Stephenson CR. J. J. Am. Chem. Soc. 2010; 132: 1464
2b Freeman DB, Furst L, Condie AG, Stephenson CR. J. Org. Lett. 2012; 14: 94
2c Zou Y.-Q, Lu L.-Q, Fu L, Chang N.-J, Rong J, Chen J.-R, Xiao W.-J. Angew. Chem. Int. Ed. 2011; 50: 7171
2d Xuan J, Cheng Y, An J, Lu L.-Q, Zhang X.-X, Xiao W.-J. Chem. Commun. 2011; 47: 8337
2e Xie Z, Wang C, de Krafft KE, Lin W. J. Am. Chem. Soc. 2011; 133: 2056
2f Zhu M, Zheng N. Synthesis 2011; 2223
2g Rueping M, Leonori D, Poisson T. Chem. Commun. 2011; 47: 9615
2h Hari DP, König B. Org. Lett. 2011; 13: 3852
2i Rueping M, Zhu S, Koenigs RM. Chem. Commun. 2011; 47: 8679
2j Rueping M, Zoller J, Fabry DC, Poscharny K, Koenigs RM, Weirich TE. Chem.–Eur. J. 2012; 18: 3478
2k Miyake Y, Nakajima K, Nishibayashi Y. J. Am. Chem. Soc. 2012; 134: 3338

For papers on C(sp³)–H functionalization using visible light photoredox catalysis via an oxidative quenching cycle, see:

3a For p-methoxybenzyl (PMB) ethers, see: Tucker JW, Narayanam JM. R, Shah PS, Stephenson CR. J. Chem. Commun. 2011; 47: 5040
3b For dialkylamides, see: Dai C, Meschini F, Narayanam JM. R, Stephenson CR. J. J. Org. Chem. 2012; 77: 4425

For representative papers on other visible light photocatalysis, see:

4a Pham PV, Nagib DA, MacMillan DW. C. Angew. Chem. Int. Ed. 2011; 50: 6119
4b McNally A, Prier CK, MacMillan DW. C. Science 2011; 334: 1114
4c Nagib DA, MacMillan DW. C. Nature 2011; 480: 224
4d Lu Z, Shen M, Yoon TP. J. Am. Chem. Soc. 2011; 133: 1162
4e Hurtley AE, Cismesia MA, Ischay MA, Yoon TP. Tetrahedron 2011; 67: 4442
4f Du J, Ruiz Espelt L, Guzei IA, Yoon TP. Chem. Sci. 2011; 2: 2115
4g Lin S, Ischay MA, Fry CG, Yoon TP. J. Am. Chem. Soc. 2011; 133: 19350
4h Zou Y.-Q, Chen J.-R, Liu X.-P, Lu L.-Q, Davis RL, Jørgensen KA, Xiao W.-J. Angew. Chem. Int. Ed. 2012; 51: 784
4i Dai C, Narayanam JM. R, Stephenson CR. J. Nat. Chem. 2011; 3: 140
4j Nguyen JD, Tucker JW, Konieczynska MD, Stephenson CR. J. J. Am. Chem. Soc. 2011; 133: 3160
4k Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS. J. Am. Chem. Soc. 2011; 133: 18566
4l Maity S, Zhu M, Shinabery RS, Zheng N. Angew. Chem. Int. Ed. 2012; 51: 222

For selected reviews on C(sp³)–H bond functionalization, see:

5a Giri R, Shi B.-F, Engle KM, Maugel N, Yu JQ. Chem. Soc. Rev. 2009; 38: 3242
5b Li C.-J. Acc. Chem. Res. 2009; 42: 335
5c Yoo W.-J, Li C.-J. Top. Curr. Chem. 2010; 292: 281
5d Wasa M, Engle KM, Yu J.-Q. Isr. J. Chem. 2010; 50: 605
5e Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
5f Newhouse T, Baran PS. Angew. Chem. Int. Ed. 2011; 50: 3362
5g Zhang S.-Y, Zhang F.-M, Tu Y.-Q. Chem. Soc. Rev. 2011; 40: 1937
5h Tobisu M, Chatani N. Angew. Chem. Int. Ed. 2006; 45: 1683
5i Campos KR. Chem. Soc. Rev. 2007; 36: 1069
5j Jazzar R, Hitce J, Renaudat A, Sofack-Kreutzer J, Baudoin O. Chem.–Eur. J. 2010; 16: 2654
5k Li H, Li B.-J, Shi Z.-J. Catal. Sci. Tech. 2011; 1: 191
5l Ramirez TA, Zhao B, Shi Y. Chem. Soc. Rev. 2012; 41: 931

For Pt, see:

6a Bajracharya GB, Pahadi NK, Gridnev ID, Yamatoto Y. J. Org. Chem. 2006; 71: 6204
6b Yang S, Li Z, Jian X, He C. Angew. Chem. Int. Ed. 2009; 48: 3999
6c Tobisu M, Nakai H, Chatani N. J. Org. Chem. 2009; 74: 5471
6d For Ru, see: Datta S, Odedra A, Liu R.-S. J. Am. Chem. Soc. 2005; 127: 11606
6e Odedra A, Datta S, Liu R.-S. J. Org. Chem. 2007; 72: 3289
6f For Rh, see: Shikanai D, Murase H, Hata T, Urabe H. J. Am. Chem. Soc. 2009; 131: 3166
6g For Pd, see: Zhao S.-C, Shu X.-Z, Ji K.-G, Zhou A.-X, He T, Liu X.-Y, Liang Y.-M. J. Org. Chem. 2011; 76: 1941
6h For Cu, see: Zeng X, Ilies L, Nakamura E. J. Am. Chem. Soc. 2011; 133: 17638
6i For Au, see: Bhunia S, Ghorpade S, Huple DB, Liu R.-S. Angew. Chem. Int. Ed. 2012; 51: 2939

For representative reviews and papers on the use of arylsulfonyl chlorides as aryl group resources, see:

7a Morrison RT, Boyd RN. Organic Chemistry . 5th ed. Allyn and Bacon; Boston: 1987
7b Dubbaka SR, Vogel P. Angew. Chem. Int. Ed. 2005; 44: 7674
7c Kasahara A, Izumi T, Kudou N, Azami H, Yamamoto S. Chem. Ind. (London) 1988; 51
7d Miura M, Hashimoto H, Itoh K, Nomura M. Tetrahedron Lett. 1989; 30: 975
7e Dubbaka SR, Vogel P. J. Am. Chem. Soc. 2003; 125: 15292
7f Dubbaka SR, Vogel P. Tetrahedron Lett. 2006; 47: 3345
7g Volla CM. R, Vogel P. Angew. Chem. Int. Ed. 2008; 47: 1305
7h Volla CM. R, Dubbaka SR, Vogel P. Tetrahedron 2009; 65: 504
7i Chen J, Sun Y, Liu B, Liu D, Cheng J. Chem. Commun. 2012; 48: 449

8a Lopes LM. X, Yoshida M, Gottlieb OR. Phytochemistry 1984; 23: 2021
8b Nagle DG, Zhou Y.-D, Park PU, Paul VJ, Rajbhandari I, Duncan CJ. G, Pasco DS. J. Nat. Prod. 2000; 63: 1431
8c Sugimoto H, Iimura Y, Yamanishi Y, Yamatsu K. J. Med. Chem. 1995; 38: 4821
8d Dolling U.-H, Davis P, Grabowski EJ. J. J. Am. Chem. Soc. 1984; 106: 446
8e deSolms SJ, Woltersdorf OW. Jr, Cragoe EJ. Jr, Watson LS, Fanelli GM. Jr. J. Med. Chem. 1978; 21: 437
8f Park CH, Siomboing X, Yous S, Gressier B, Luyckx M, Chavatte P. Eur. J. Med. Chem. 2002; 37: 461
8g Anstead GM, Wilson SR, Katzenellenbogen JA. J. Med. Chem. 1989; 32: 2163
8h Hajela K, Kapil RS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1995; 34: 361
8i Alcalde E, Mesquida N, López-Pérez S, Frigola J, Mercè R. J. Med. Chem. 2009; 52: 675
8j Ito T, Tanaka T, Iinuma M, Nakaya K, Takahashi Y, Sawa R, Murata J, Darnaedi D. J. Nat. Prod. 2004; 67: 932

9 Typical Experimental Procedure for the Arylative Cyclization of ortho-Alkyl Arylalkynes with Arylsulfonyl Chlorides: To a Schlenk tube were added ortho-alkyl arylalkyne 1 (0.2 mmol), arylsulfonyl chloride 2 (3 equiv), [Ru(bpy)₃Cl₂] or [Ir(ppy)₃] (3 mol%), Na₂CO₃ (2.5 equiv), and anhydrous MeCN (1 mL). The tube was charged with argon and stirred at 45 °C under irradiation with a 36 W compact fluorescent light for the indicated time (36 h) until complete consumption of starting material (reaction monitored by TLC and GC–MS analysis). When the reaction was finished, the mixture was diluted in diethyl ether, filtered through a short crude silica gel column and concentrated under vacuum. The resulting residue was purified by silica gel column chromatography (hexane–ethyl acetate) to afford the desired product. 1,1-Dimethyl-3-(4-nitrophenyl)-2-phenyl-1H-indene (3): Yield: 55.7 mg (83%); yellow solid; mp 128.7–129.5 °C (uncorrected); ¹H NMR (500 MHz, CDCl₃): δ = 8.12 (d, J = 8.5 Hz, 2 H), 7.47–7.43 (m, 3 H), 7.32–7.29 (m, 6 H), 7.13–7.11 (m, 2 H), 1.42 (s, 6 H); ¹³C NMR (125 MHz, CDCl₃): δ = 156.0, 153.0, 146.6, 142.3, 141.4, 136.1, 135.7, 130.2, 129.5, 128.3, 127.5, 126.8, 126.0, 123.4, 121.9, 120.2, 51.9, 24.3; MS (EI, 70 eV): m/z (%) = 341 (100) [M]⁺, 326 (46), 279 (15), 132 (8); HRMS (EI): m/z [M]⁺ calcd for C₂₃H₁₉NO₂: 341.1415; found: 341.1411.

10a Masamune S, Sakai M, Morio K. Can. J. Chem. 1975; 53: 784
10b Hanack M. Acc. Chem. Res. 1976; 9: 364
10c Dicoordinated Carbocations . Rappoport Z, Stang PJ. John Wiley & Sons; Chichester: 1997
10d Okuyama T. Acc. Chem. Res. 2002; 35: 12
10e Okuyama T, Lodder G In Advances in Physical Organic Chemistry . Tidwell TT, Richard JP. Elsevier; Amsterdam: 2002: 1-56

Zusatzmaterial

Supporting Information