Metal-Free Oxidative Coupling of Tetrahydroisoquinolines and 3-Fluorooxindoles on Water

Jian Ji; Ling-Yan Chen; Zi-Bin Qiu; Xinfeng Ren; Ya Li

doi:10.1055/s-0039-1690213

Synthesis, Table of Contents

Synthesis 2020; 52(03): 471-478
DOI: 10.1055/s-0039-1690213

paper

Metal-Free Oxidative Coupling of Tetrahydroisoquinolines and 3-Fluorooxindoles on Water

Authors

Jian Ji
Ling-Yan Chen ∗
Zi-Bin Qiu
Xinfeng Ren
Ya Li∗

Abstract

All articles of this category

Abstract

An efficient, metal-free oxidative coupling of tetrahydroisoquinolines and 3-fluorooxindoles on water has been developed. Using aqueous tert-butyl hydroperoxide as the oxidant, Et₃N as the base, and water as the sole solvent, a variety of 3-fluorooxindoles fully substituted at the 3-position and containing a tetrahydroisoquinoline fragment has been successfully prepared in yields of up to 93% with an anti/syn stereoselectivity of up to 99:1 under very mild and safe reaction conditions.

Key words

fluorine - fluoroalkylation - oxidative coupling - water - green synthesis

Full Text

References

References

1a Bégué JP, Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine . Wiley-VCH; Hoboken: 2008
1b Zhou Y, Wang J, Gu Z, Wang S, Zhu W, Aceña JL, Soloshonok VA, Izawa K, Liu H. Chem. Rev. 2016; 116: 422

2a Cao Z.-Y, Zhou F, Zhou J. Acc. Chem. Res. 2018; 51: 1443
2b Cao Z.-Y, Wang Y.-H, Zeng X.-P, Zhou J. Tetrahedron Lett. 2014; 55: 2571
2c Dalpozzo R. Org. Chem. Front. 2017; 4: 2063

3a Gribkoff VK, Starrett JE. Jr, Dworetzky SI, Hewawasam P, Boissard CG, Cook DA, Frantz SW, Heman K, Hibbard JR, Huston K, Johnson G, Krishnan BS, Kinney GG, Lombardo LA, Meanwell NA, Molinoff PB, Myers RA, Moon SL, Ortiz A, Pajor L, Pieschl RL, Post-Munson DJ, Signor LJ, Srinivas N, Taber MT, Thalody G, Trojnacki JT, Wiener H, Yeleswaram K, Yeola SW. Nat. Med. 2001; 7: 471
3b Cheney JA, Weisser JD, Bareyre FM, Laurer HL, Saatman KE, Raghupathi R, Gribkoff V, Starrett JE. Jr, McIntosh TK. J. Cereb. Blood Flow Metab. 2001; 21: 396

For selected examples, see:

4a Li J, Cai Y, Chen W, Liu X, Lin L, Feng X. J. Org. Chem. 2012; 77: 9148
4b Shibata N, Ishimaru T, Suzuki E, Kirk KL. J. Org. Chem. 2003; 68: 2494
4c Hamashima Y, Suzuki T, Takano H, Shimura Y, Sodeoka M. J. Am. Chem. Soc. 2005; 127: 10164
4d Zhang R, Wang D, Xu Q, Jiang J, Shi M. Chin. J. Chem. 2012; 30: 1295
4e Zoute L, Audouard C, Plaquevent J.-C, Cahard D. Org. Biomol. Chem. 2003; 1: 1833
4f Gu X, Zhang Y, Xu Z.-J, Che C.-M. Chem. Commun. 2014; 50: 7870
4g Ishimaru T, Shibata N, Horikawa T, Yasuda N, Nakamura S, Toru T, Shiro M. Angew. Chem. Int. Ed. 2008; 47: 4157
4h Zhu C.-L, Maeno M, Zhang F.-G, Shigehiro T, Kagawa T, Kawada K, Shibata N, Ma J.-A. Eur. J. Org. Chem. 2013; 6501

For selected examples, see:

5a Dou X, Lu Y. Org. Biomol. Chem. 2013; 11: 5217
5b Balaraman K, Wolf C. Angew. Chem. Int. Ed. 2017; 56: 1390
5c Wang T, Hoon DL, Lu Y. Chem. Commun. 2015; 51: 10186
5d Paladhi S, Park SY, Yang JW, Song CE. Org. Lett. 2017; 19: 5336
5e Jin Y, Chen M, Ge S, Hartwig JF. Org. Lett. 2017; 19: 1390
5f Ding R, Wolf C. Org. Lett. 2018; 20: 892
5g Balaraman K, Ding R, Wolf C. Adv. Synth. Catal. 2017; 359: 4165
5h Moskowitz M, Balaraman K, Wolf C. J. Org. Chem. 2018; 83: 1661

For selected examples on the use of 3-fluoro-3-(2,2,2-trifluoro-1,1-dihydroxyethyl)indolin-2-one as the starting material, see:

6a Zhu Y, Mao Y, Mei H, Pan Y, Han J, Soloshonok VA, Hayashi T. Chem. Eur. J. 2018; 24: 8994
6b Zhu Y, Mei H, Han J, Soloshonok VA, Zhou J, Pan Y. J. Org. Chem. 2017; 82: 13663
6c Xie C, Zhang L, Sha W, Soloshonok VA, Han J, Pan Y. Org. Lett. 2016; 18: 3270
6d Zhang W, Sha W, Zhu Y, Han J, Soloshonok VA, Pan Y. Eur. J. Org. Chem. 2017; 1540
6e Zhang L, Zhang W, Mei H, Han J, Soloshonok VA, Pan Y. Org. Biomol. Chem. 2017; 15: 311
6f Xie C, Sha W, Zhu Y, Han J, Soloshonok VA, Pan Y. RSC Adv. 2017; 7: 5679

For selected reviews: see:

7a Le VH, Inai M, Williams RM, Kan T. Nat. Prod. Rep. 2015; 32: 328
7b Sridharan V, Suryavanshi PA, Menendez JC. Chem. Rev. 2011; 111: 7157
7c Siengalewicz P, Rinner U, Mulzer J. Chem. Soc. Rev. 2008; 37: 2676

For reviews, see:

8a Girard SA, Thomas K, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
8b Scheuermann CJ. Chem. Asian J. 2010; 5: 436
8c Li C.-J. Acc. Chem. Res. 2009; 42: 335

For the very recent examples on the C1-functionaliziation of tetrahydroisoquinoline through the CDC reaction, see:

9a Džambaskia Z, Bondžić BP. Org. Biomol. Chem. 2019; 17: 6420
9b Gil-Negrete JM, Sestelo JP, Sarandeses LA. J. Org. Chem. 2019; 84: 9778
9c Li B, Wendlandt AE, Stahl SS. Org. Lett. 2019; 21: 1176
9d Xu C, Zhu Z, Wang Y, Jing Z, Gao B, Zhao L, Dong W.-K. J. Org. Chem. 2019; 84: 2234

10a Chu L, Qing F.-L. Chem. Commun. 2010; 46: 6285
10b Fu W, Guo W, Zou G, Xu C. J. Fluorine Chem. 2012; 140: 88
10c Mitsudera H, Li C.-J. Tetrahedron Lett. 2011; 52: 1898

11 Chu L, Zhang X, Qing F.-L. Org. Lett. 2009; 11: 2197
12 Chen Q, Zhou J, Wang Y, Wang C, Liu X, Xu Z, Lin L, Wang R. Org. Lett. 2015; 17: 4212

13a Li W, Zhu Y, Duan Y, Zhang M, Zhu C. Adv. Synth. Catal. 2015; 357: 1277
13b Li W, Zhu X, Mao H, Tang Z, Cheng Y, Zhu C. Chem. Commun. 2014; 50: 7521

14 Punirun T, Soorukram D, Kuhakarn C, Reutrakul V, Pohmakotr M. J. Org. Chem. 2018; 83: 765
15 Shirley LD, Ceban V, Meazza M, Rios R. ChemistrySelect 2016; 1: 13
16 Ji J, Chen L.-Y, Qiu Z.-B, Ren X, Li Y. Asian J. Org. Chem. 2019; 8: 1436

17a Zhao J.-B, Li Y, Chen L.-Y, Ren X. J. Org. Chem. 2019; 84: 5099
17b Chen X, Li Y, Zhao J.-B, Zheng B.-Q, Lu Q, Ren X. Adv. Synth. Catal. 2017; 359: 3057
17c Zheng B.-Q, Chen L.-Y, Zhao J.-B, Ji J, Qiu Z.-B, Ren X, Li Y. Org. Biomol. Chem. 2018; 16: 8989

18a Tsang AS.-K, Todd MH. Tetrahedron Lett. 2009; 50: 1199
18b Wang HLi X, Wu F, Wan B. Tetrahedron Lett. 2012; 53: 681

19a Mudithanapelli C, Dhorma LP, Kim Mi-h. Org. Lett. 2019; 21: 3098
19b Kumar RA, Saidulu G, Prasad KR, Kumar GS, Sridhar B, Reddya KR. Adv. Synth. Catal. 2012; 354: 2985
19c Fang L, Li Z, Jiang Z, Tan Z, Xie Y. Eur. J. Org. Chem. 2016; 3559

For examples of metal-catalyzed oxidative coupling of tetrahydroisoquinolines in water, see:

20a Baslé O, Li C.-J. Green Chem. 2007; 9: 1047
20b Alagiri K, Kumara GS. R, Prabhu KR. Chem. Commun. 2011; 47: 11787
20c Meng Q.-Y, Liu Q, Zhong J.-J, Zhang H.-H, Li Z.-J, Chen B, Tung C.-H, Wu L.-Z. Org. Lett. 2012; 14: 5992
20d Wu C.-J, Zhong J.-J, Meng Q.-Y, Lei T, Gao X.-W, Tung C.-H, Wu L.-Z. Org. Lett. 2015; 17: 884
20e Zhang Y, Wei B.-W, Wang W.-X, Deng L.-L, Nie L.-J, Luo H.-Q, Fan X.-L. RSC Adv. 2017; 7: 1229

21a Rao GA, Periasamy M. Synthesis 2018; 50: 617
21b Lin B, Lu G, Lin R, Cui Y, Liu Y, Tang G, Zhao Y. Synlett 2018; 29: 2697
21c Zhang Z, Gu K, Bao Z, Xing H, Yang Q, Ren Q. Tetrahedron 2017; 73: 3118

Supplementary Material

Supporting Information (PDF)