Synthesis of β-Selenylated Cyclopentanones via Photoredox-Catalyzed Selenylation/Ring-Expansion Cascades of Alkenyl Cyclobutanols

Hye Im Jung; Dae Young Kim

doi:10.1055/s-0037-1611841

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(11): 1361-1365
DOI: 10.1055/s-0037-1611841

letter

Synthesis of β-Selenylated Cyclopentanones via Photoredox-Catalyzed Selenylation/Ring-Expansion Cascades of Alkenyl Cyclobutanols

Autor*innen

Hye Im Jung
Dae Young Kim *

Department of Chemistry, Soonchunhyang University, Asan, Chungnam 31538, Republic of Korea eMail: dyoung@sch.ac.kr

Abstract

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Abstract

A photoredox strategy to access β-selenated cyclic ketone derivatives through the coupling reaction of 1-(1-arylvinyl)cyclobutanols with diselenides under blue LED irradiation and an air atmosphere was developed. This reaction employs the easily accessible and shelf-stable diselenides as a selenium radical source, and the reaction has advantages of mild reaction conditions and broad substrate scope.

Key words

selenylation - semipinacol rearrangement - 1,2-alkyl migration - 1-(1-arylvinyl)cyclobutanols - photoredox reaction

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Referenzen

References and Notes

1a Mugesh G, Singh HB. Acc. Chem. Res. 2002; 35: 226
1b Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255
1c Kumar S, Johansson H, Kanda T, Engman L, Müller T, Bergenudd H, Jonsson M, Pedulli GF, Amorati R, Valgimigli L. J. Org. Chem. 2010; 75: 716
1d Sarma BK, Manna D, Minoura M, Mugesh G. J. Am. Chem. Soc. 2010; 132: 5364
1e Santi C. In Organoselenium Chemistry Between Synthesis and Biochemistry. Bentham Science; Sharjah: 2014
1f Sancineto L, Mariotti A, Bagnoli L, Marini F, Desantis J, Iraci N, Santi C, Pannecouque C, Tabarrini O. J. Med. Chem. 2015; 58: 9601
1g Mondal S, Manna D, Mugesh G. Angew. Chem. Int. Ed. 2015; 54: 9298
1h Pang Y, An B, Lou L, Zhang J, Yan J, Huang L, Li X, Yin S. J. Med. Chem. 2017; 60: 7300
1i Kumar S, Johansson H, Kanda T, Engman L, Müller T, Bergenudd H, Jonsson M. Eur. J. Org. Chem. 2017; 3055

2a Silveira CC, Braga AL, Vieira AS, Zeni G. J. Org. Chem. 2003; 68: 662
2b Kundu D, Ahammed S, Ranu BC. Org. Lett. 2014; 16: 1814
2c Luo J, Zhu Z, Liu Y, Zhao X. Org. Lett. 2015; 17: 3620
2d Verma A, Jana S, Prasad CD, Yadav A, Kumar S. Chem. Commun. 2016; 52: 4179

3a Zeni G, Ludtke DS, Panatieri RB, Braga AL. Chem. Rev. 2006; 106: 1032
3b Perin G, Lenardao EJ, Jacob RG, Panatieri RB. Chem. Rev. 2009; 109: 1277
3c Freudendahl DM, Santoro S, Shahzad SA, Santi C, Wirth T. Angew. Chem. Int. Ed. 2009; 48: 8409
3d Abdo M, Zhang Y, Schramm VL, Knapp S. Org. Lett. 2010; 12: 2982
3e Rafique J, Saba S, Rosario AR, Braga AL. Chem. Eur. J. 2016; 22: 11854
3f Shu S, Fan Z, Yao Q, Zhang A. J. Org. Chem. 2016; 81: 5263
3g Sun K, Wang X, Lv Y, Li G, Jiao H, Dai C, Li Y, Zhanga C, Liu L. Chem. Commun. 2016; 52: 8471

Reviews for reactions with diselenides, see:

4a Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
4b Ivanova A, Arsenyan P. Coord. Chem. Rev. 2018; 370: 55

For selected examples for the reaction of diselenides with various substrates, see:

4c Zheng Y, He Y, Rong G, Zhang X, Weng Y, Dong K, Xu X, Mao J. Org. Lett. 2015; 17: 5444
4d Sun J, Zhang-Negrerie D, Du Y. Adv. Synth. Catal. 2016; 358: 2035
4e Qiu J.-K, Shan C, Wang D.-C, Wei P, Jiang B, Tu S.-J, Li G, Guo K. Adv. Synth. Catal. 2017; 359: 4332
4f Zhu Y.-Q, He J.-L, Niu Y.-X, Kang H.-Y, Han T.-F, Li H.-Y. J. Org. Chem. 2018; 83: 9958
4g Liu Y, Li C, Mu S, Li Y, Feng R, Sun K. Asian J. Org. Chem. 2018; 7: 720
4h Yu J.-M, Cai C. Org. Biomol. Chem. 2018; 16: 490
4i Zhao F, Sun T, Liu Z, Sun K, Zhang C, Wang X. Curr. Org. Chem. 2018; 22: 613
4j Wu P, Wu K, Wang L, Yu Z. Org. Lett. 2017; 19: 5450
4k Ricordi VG, Freitas CS, Perin G, Lenardão EJ, Jacob RG, Savegnago L, Alves D. Green Chem. 2012; 14: 1030
4l Zheng B, Gong Y, Xu H.-J. Tetrahedron 2013; 69: 5342
4m Kumar A, Kumar S. Tetrahedron 2014; 70: 1763
4n Jana S, Chakraborty A, Mondal S, Hajra A. RSC Adv. 2015; 5: 77534
4o Ricordi VG, Thurow S, Penteado F, Schumacher RF, Perin G, Lenardão EJ, Alves D. Adv. Synth. Catal. 2015; 357: 933
4p Yu S, Wan B, Li X. Org. Lett. 2015; 17: 58
4q Ferreira NL, Azeredo JB, Fiorentin BL, Braga AL. Eur. J. Org. Chem. 2015; 23: 5070
4r Mandal A, Sahoo H, Baidya M. Org. Lett. 2016; 18: 3202
4s Sahoo H, Mandal A, Selvakumar J, Baidya M. Eur. J. Org. Chem. 2016; 25: 4321
4t Gandeepan P, Koeller J, Ackermann L. ACS Catal. 2017; 7: 1030
4u Kibriya G, Samanta S, Singsardar M, Jana S, Hajra A. Eur. J. Org. Chem. 2017; 3055
4v Zhang Q.-B, Ban Y.-L, Yuan P.-F, Peng S.-J, Fang J.-G, Liu L.-ZW. Q. Green Chem. 2017; 19: 5559
4w Saba S, Rafique J, Franco MS, Schneider AR, Espíndola L, Silva DO, Brag AL. Org. Biomol. Chem. 2018; 16: 880
4x Kumaraswamy G, Ramesh V, Gangadhar M, Vijaykumar S. Asian J. Org. Chem. 2018; 7: 1689

Selected recent reviews for difunctionalization of alkenes, see:

5a Sha W, Deng L, Ni S, Mei H, Han J, Pan Y. ACS Catal. 2018; 8: 7489
5b Zhang Y.-X, Jin R.-X, Yin H, Li Y, Wang X.-S. Org. Lett. 2018; 20: 7283
5c Nakafuku KM, Fosu SC, Nagib DA. J. Am. Chem. Soc. 2018; 140: 11202

Reviews for semipinacol-type rearrangement, see:

5d Song ZL, Fan CA, Tu YQ. Chem. Rev. 2011; 111: 7523
5e Wang B, Tu YQ. Acc. Chem. Res. 2011; 44: 1207
5f Wang SH, Li BS, Tu YQ. Chem. Commun. 2014; 50: 2393
5g Chen ZM, Zhang XM, Tu YQ. Chem. Soc. Rev. 2015; 44: 5220

Selected recent examples, see:

6a Zhang E, Fan CA, Tu YQ, Zhang FM, Song YL. J. Am. Chem. Soc. 2009; 131: 14626
6b Zhang QW, Fan CA, Zhang HJ, Tu YQ, Zhao YM, Gu P, Chen ZM. Angew. Chem. Int. Ed. 2009; 48: 8572
6c Romanov-Michailidis F, Guénée L, Alexakis A. Angew. Chem. Int. Ed. 2013; 52: 9266
6d Yin Q, You SL. Org. Lett. 2014; 16: 1810
6e Xu MH, Dai KL, Tu YQ, Zhang XM, Zhanga FM, Wanga SH. Chem. Commun. 2018; 54: 7685
6f Xi CC, Chen ZM, Zhang SY, Tu YQ. Org. Lett. 2018; 20: 4227

Review for radical-mediated 1,2-migration of allyl alcohols, see:

7a Weng W.-Z, Zhang B. Chem. Eur. J. 2018; 24: 10934

For selected examples, see:

7b Shu XZ, Zhang M, He Y, Frei H, Toste FD. J. Am. Chem. Soc. 2014; 136: 5844
7c Sahoo B, Li JL, Glorius F. Angew. Chem. Int. Ed. 2015; 54: 11577
7d Suh CW, Kim DY. Tetrahedron Lett. 2015; 56: 5661
7e Woo SB, Kim DY. J. Fluorine Chem. 2015; 178: 214
7f Kwon SJ, Kim YJ, Kim DY. Tetrahedron Lett. 2016; 57: 4371
7g Kwon SJ, Kim DY. Org. Lett. 2016; 18: 4562
7h Kim YJ, Kim DY. J. Fluorine Chem. 2018; 211: 119
7i Kim YJ, Choo MH, Kim DY. Tetrahedron Lett. 2018; 59: 3864
7j Kim YJ, Kim DY. Org. Lett. 2019; 21: 1021
7k Jung HI, Kim Y, Kim DY. Org. Biomol. Chem. 2019; 17: 3319
7l Kim Y, Kim DY. Asian J. Org. Chem. 2019; 8: 679
7m Kim YJ, Kim DY. Tetrahedron Lett. 2019; 60: 1287
7n Honeker R, Sanchez RA. G, Hopkinson MN, Glorius F. Chem. Eur. J. 2016; 22: 4395
7o Bergonzini G, Cassani C, Olsson HL, Hörberg J, Wallentin CJ. Chem. Eur. J. 2016; 22: 3292
7p Weng WZ, Sun JG, Li P, Zhang B. Chem. Eur. J. 2017; 23: 9752
7q Zhang JJ. Chin. J. Chem. 2017; 35: 311
7r Wu H, Wang Q, Zhu J. Chem. Eur. J. 2017; 23: 13037
7s Yao S, Zhang K, Zhou QQ, Zhao Y, Shi DQ, Xiao WJ. Chem. Commun. 2018; 54: 8096

For representative recent reviews and papers for photocatalysis, see:

8a Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527
8b Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
8c Maity S, Zheng N. Synlett 2012; 23: 1851
8d Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
8e Xuan J, Xiao W.-J. Angew. Chem. Int. Ed. 2012; 51: 6828
8f Maity S, Zheng N. Synlett 2012; 23: 1851
8g Xi Y.-M, Yi H, Lei A.-W. Org. Biomol. Chem. 2013; 11: 2387
8h Prier CK, Rankic DA, MacMillan DW. Chem. Rev. 2013; 113: 5322
8i Schultz DM, Yoon TP. Science 2014; 343: 985
8j Koike T, Akita M. Top. Catal. 2014; 57: 967
8k Hopkinson MN, Sahoo B, Li J.-L, Glorius F. Chem. Eur. J. 2014; 20: 3874
8l Koike T, Akita M. Inorg. Chem. Front. 2014; 1: 562
8m Majek M, Filace F, Wangelin AJ. Beilstein J. Org. Chem. 2014; 10: 981
8n Meggers E. Chem. Commun. 2015; 51: 3290
8o Cismesia MA, Yoon TP. Chem. Sci. 2015; 6: 5426
8p Angnes RA, Li Z, Correia CR. D, Hammond GB. Org. Biomol. Chem. 2015; 13: 9152
8q Shaw MH, Twilton J, MacMillan DW. C. J. Org. Chem. 2016; 81: 6898
8r Ravelli D, Protti S, Fagnoni M. Chem. Rev. 2016; 116: 9850
8s Kärkäs MD, Porco JA. Jr, Stephenson CR. J. Chem. Rev. 2016; 116: 9683
8t Garbarino S, Ravelli D, Protti S, Basso A. Angew. Chem. Int. Ed. 2016; 55: 15476
8u Matsui JK, Lang SB, Heitz DR, Molander GA. ACS. Catal. 2017; 7: 2564
8v Bogdos MK, Pinard E, Murphy JA. Beilstein J. Org. Chem. 2018; 14: 2035

For a selection of our recent work on C–H activation, see:

9a Kang YK, Kim SM, Kim DY. J. Am. Chem. Soc. 2010; 132: 11847
9b Kang YK, Kim DY. Adv. Synth. Catal. 2013; 355: 3131
9c Suh CW, Woo SB, Kim DY. Asian J. Org. Chem. 2014; 3: 399
9d Kang YK, Kim DY. Chem. Commun. 2014; 50: 222
9e Suh CW, Kim DY. Org. Lett. 2014; 16: 5374
9f Kwon SJ, Kim DY. Chem. Rec. 2016; 16: 1191
9g Suh CW, Kwon SJ, Kim DY. Org. Lett. 2017; 19: 1334
9h Jeong HJ, Kim DY. Org. Lett. 2018; 20: 2944

10a Dowd P, Choi S.-C. J. Am. Chem. Soc. 1987; 109: 3493
10b Dowd P, Choi S.-C. J. Am. Chem. Soc. 1987; 109: 6548
10c Beckwith AL. J, O’Shea DM, Westwood SW. J. Chem. Soc., Chem. Commun. 1987; 666
10d Beckwith AL. J, O’Shea DM, Westwood SW. J. Am. Chem. Soc. 1988; 110: 2565
10e Shono T, Kise N, Uematsu N, Morimoto S, Okazaki E. J. Org. Chem. 1990; 55: 5037
10f Dowd P, Zhang W. Chem. Rev. 1993; 93: 2091
10g Hasegawa E, Mori K, Tsuji S, Nemoto K, Ohta T, Iwamoto H. Aust. J. Chem. 2015; 68: 1648
10h Hasegawa E, Nemoto K, Nagumo R, Tayama E, Iwamoto H. J. Org. Chem. 2016; 81: 2692
10i Liu Y, Yeung Y.-Y. Org. Lett. 2017; 19: 1422

11a Ogawa A, Obayashi R, Doi M, Sonoda N, Hirao T. J. Org. Chem. 1998; 63: 4277
11b Pandey G, Gadre SR. Acc. Chem. Res. 2004; 37: 201
11c Zhang Q.-B, Ban Y.-L, Yuan P.-F, Peng S.-J, Fang J.-G, Wu L.-Z, Liu Q. Green Chem. 2017; 19: 5559
11d Sahoo H, Mandal A, Dana S, Baidya M. Adv. Synth. Catal. 2018; 360: 1099

12 General Procedure for Photoredox Selenylation/Ring-Expansion Sequences of Alkenyl Cyclobutanols An oven-dried flask equipped with a magnetic stir bar was charged with 1-(1-arylvinyl)cyclobutanols 1 (0.1 mmol), diselenide 2 (0.06 mmol), Ru(bpy)₃Cl₂·6H₂O (2.2 mg, 3 μmol), and acetonitrile (1 mL) under air. The reaction mixture was stirred for 8–25 h under irradiation of blue LEDs (5 W, 455 nm). The reaction mixture was concentrated under vacuum and purified by chromatography on silica gel (ethyl acetate/n-hexane = 1:20) to afford β-selenated cyclic ketone derivatives 3.
13 2-Phenyl-2-[(phenylselanyl)methyl]cyclopentanone (3a) Yield 83%; yellow oil. ¹H NMR (400 MHz, CDCl₃): δ = 7.42–7.37 (m, 4 H), 7.34–7.30 (m, 2 H), 7.27–7.23 (m, 1 H), 7.21–7.18 (m, 3 H), 3.39 (d, J = 12 Hz, 1 H), 3.30 (d, J = 12.4 Hz, 1 H), 2.70–2.65 (m, 1 H), 2.40–2.20 (m, 3 H), 2.00–1.90 (m, 1 H), 1.84–1.73 (m, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 217.9, 138.4, 132.6, 131.0, 128.9, 128.7, 127.4, 126.8, 126.7, 57.8, 37.8, 37.4, 33.6, 18.4. HRMS (ESI): m/z calcd for C₁₈H₁₈OSe [M]⁺ : 330.0523; found: 330.0527.

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