Lewis Base Promoted, Direct 1,4-Conjugate Addition to Quinone Imine Ketals: Efficient Access to Unsymmetrical Diaryl Sulfones

Teng Liu; Jianjun Liu; Xianfu Shen; Jianbin Xu; Beifang Nian; Ni He; Shunqun Zeng; Feixiang Cheng

doi:10.1055/s-0037-1610317

Synthesis, Table of Contents

Synthesis 2019; 51(06): 1365-1376
DOI: 10.1055/s-0037-1610317

paper

Lewis Base Promoted, Direct 1,4-Conjugate Addition to Quinone Imine Ketals: Efficient Access to Unsymmetrical Diaryl Sulfones

Teng Liu*

Center for Yunnan-Guizhou Plateau Chemical Functional Materials and Pollution Control, Qujing Normal University, Qujing 655011, P. R. of China

,

Jianjun Liu

,

Xianfu Shen

,

Jianbin Xu

,

Beifang Nian

,

Ni He

,

Shunqun Zeng

,

Feixiang Cheng*

Center for Yunnan-Guizhou Plateau Chemical Functional Materials and Pollution Control, Qujing Normal University, Qujing 655011, P. R. of China

› Author Affiliations

Abstract

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^‡ New address: College of Materials and Chemical Engineering, Pingxiang University, Pingxiang 337055, China 15288404381@163.com

Abstract

An alternative approach with eco-friendliness and high efficiency for the preparation of unsymmetrical diaryl sulfones has been developed. The strategy takes advantage of the reaction of sulfonyl hydrazides with quinone imine ketals catalyzed by DABCO (triethylenediamine) in ethanol. This transformation proceeds via a Lewis base promoted, direct 1,4-conjugate addition/sulfonylation/alcohol elimination reaction sequence. The protocol provides an efficient approach to access an array of diverse unsymmetrical diaryl and heterodiaryl sulfones, aryl alkyl sulfones and aryl vinyl sulfones in good to excellent yields.

Key words

unsymmetrical diaryl sulfones - eco-friendliness - Lewis base - 1,4-conjugate addition - quinone imine ketals

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References

References

1a Carreno MC. Chem. Rev. 1995; 95: 1717
1b Teall M, Oakley P, Harrison T, Shaw D, Kay E, Elliott J, Gerhard U, Castro JL, Shearman M, Ball RG, Tsou NN. Bioorg. Med. Chem. Lett. 2005; 15: 2685
1c Bentley R. Chem. Soc. Rev. 2005; 34: 609
1d Meadows DC, Sanchez T, Neamati N, North TW, Gervay-Hague J. Bioorg. Med. Chem. 2007; 15: 1127
1e Ladduwahetty T, Gilligan M, Humphries A, Merchant KJ, Fish R, McAlister G, Ivarsson M, Dominguez M, O’Connor D, MacLeod AM. Bioorg. Med. Chem. Lett. 2010; 20: 3708

2a Simpkins NS. Sulfones in Organic Synthesis . Pergamon Press; Oxford: 1993
2b Bhanuchandra M, Yorimitsu H, Osuka A. Org. Lett. 2016; 18: 384
2c Ariki ZT, Maekawa Y, Nambo M, Crudden CM. J. Am. Chem. Soc. 2018; 140: 78
2d Takahashi F, Nogi K, Yorimitsu H. Org. Lett. 2018; 20: 6601

3a Kim DH, Lee J, Lee A. Org. Lett. 2018; 20: 764
3b Guilbaud J, Labonde M, Selmi A, Kammoun M, Cattey H, Pirio N, Roger J, Hierso J.-C. Catal. Commun. 2018; 111: 52

4a Fernández I, Khiar N. Chem. Rev. 2003; 103: 3651
4b Dybtsev DN, Nuzhdin AL, Chun H, Bryliakov KP, Talsi EP, Fedin VP, Kim K. Angew. Chem. Int. Ed. 2006; 45: 916
4c Nisar A, Lu Y, Zhuang J, Wang X. Angew. Chem. Int. Ed. 2011; 50: 3187

5a Lhoták P, Svoboda J, Stibor I. Tetrahedron 2006; 62: 1253
5b Clayden J, Senior J, Helliwell M. Angew. Chem. Int. Ed. 2009; 48: 6270
5c Wang M, Chen S, Jiang X. Org. Lett. 2017; 19: 4916

6a Cacchi S, Fabrizi G, Goggiamani A, Parisi LM, Bernini R. J. Org. Chem. 2004; 69: 5608
6b Yadav JS, Reddy BV. S, Swamy T, Ramireddy N. Synthesis 2004; 1849
6c Umierski N, Manolikakes G. Org. Lett. 2013; 15: 188
6d Konovalova SA, Avdeenko AP, Santalova AA, D’yakonenko VV, Palamarchuk GV, Shishkin OV. Russ. J. Org. Chem. 2014; 50: 1757
6e Nandi GC. Synth. Commun. 2017; 47: 319
6f Xing B, Ni C, Hu J. Chin. J. Chem. 2018; 36: 206
6g Liu N.-W, Liang S, Margraf N, Shaaban S, Luciano V, Drost M, Manolikakes G. Eur. J. Org. Chem. 2018; 1208
6h Zhou Y, Cao W.-B, Zhang L.-L, Xu X.-P, Ji S.-J. J. Org. Chem. 2018; 83: 6056
6i Smith JD, Ansari TN, Andersson MP, Dongari Y, Ibrahim F, Liang S, Hammond GB, Gallou F, Handa S. Green Chem. 2018; 20: 1784
6j Chen F, Chacón-Huete F, El-Husseini H, Forgione P. Synthesis 2018; 50: 1914
6k Xie L.-Y, Peng S, Liu F, Chen G.-R, Xia W, Yu X, Li W.-F, Cao Z, He W.-M. Org. Chem. Front. 2018; 5: 2604

7a Bandgar BP, Bettigeri SV, Phopase J. Org. Lett. 2004; 6: 2105
7b Jang DO, Moon KS, Cho DH, Kim J.-G. Tetrahedron Lett. 2006; 47: 6063
7c Cooke M, Clark J, Breeden S. J. Mol. Catal. A: Chem. 2009; 303: 132
7d Hu F, Lei X. ChemCatChem 2015; 7: 1539
7e Liang H.-W, Jiang K, Ding W, Yuan Y, Shuai L, Chen Y.-C, Wei Y. Chem. Commun. 2015; 51: 16928
7f Wei J, Jiang J, Xiao X, Lin D, Deng Y, Ke Z, Jiang H, Zeng W. J. Org. Chem. 2016; 81: 946
7g Fu Y, Xu Q.-S, Li Q.-Z, Du Z, Wang K.-H, Huang D, Hu Y. Org. Biomol. Chem. 2017; 15: 2841

8a Emmett EJ, Hayter BR, Willis MC. Angew. Chem. Int. Ed. 2013; 52: 12679
8b Deeming AS, Russell CJ, Hennessy AJ, Willis MC. Org. Lett. 2014; 16: 150
8c Emmett EJ, Hayter BR, Willis MC. Angew. Chem. Int. Ed. 2014; 53: 10204
8d Rocke BN, Bahnck KB, Herr M, Lavergne S, Mascitti V, Perreault C, Polivkova J, Shavnya A. Org. Lett. 2014; 16: 154
8e Liu T, Zhou W, Wu J. Org. Lett. 2017; 19: 6638
8f Chen Y, Willis MC. Chem. Sci. 2017; 8: 3249
8g Yang D, Sun P, Wei W, Liu F, Zhang H, Wang H. Chem. Eur. J. 2018; 24: 4423
8h Xia H, An Y, Zeng X, Wu J. Org. Chem. Front. 2018; 5: 366
8i Zhou K, Chen M, Yao L, Wu J. Org. Chem. Front. 2018; 5: 371

9a Gund SH, Shelkara RS, Nagarkar JM. RSC Adv. 2015; 5: 62926
9b Liang S, Liu N.-W, Manolikakes G. Adv. Synth. Catal. 2016; 358: 159

10a Yue H, Zhu C, Rueping M. Angew. Chem. Int. Ed. 2018; 57: 1371
10b Liu N.-W, Hofman K, Herbert A, Manolikakes G. Org. Lett. 2018; 20: 760
10c Cabrera-Afonso MJ, Lu Z.-P, Kelly CB, Lang SB, Dykstra R, Gutierrez O, Molander GA. Chem. Sci. 2018; 9: 3186
10d Muralirajan K, Kancherla R, Rueping M. Angew. Chem. Int. Ed. 2018; 57: 14787

11 Avdeenko AP, Evgrafova NI. Zh. Org. Khim. 1992; 28: 1479

12a Wu X, Wang Y. Synlett 2014; 25: 1163
12b Fu R, Hao W.-J, Wu Y.-N, Wang N.-N, Tu S.-J, Li G, Jiang B. Org. Chem. Front. 2016; 3: 1452
12c Chen G, Zhang X, Zeng Z, Peng W, Liang Q, Liu J. ChemistrySelect 2017; 2: 1979
12d Li P.-G, Li Y.-C, Zhu T, Zou L.-H, Wu Z. Eur. J. Org. Chem. 2017; 6081
12e Wu X, Wang Y. New J. Chem. 2018; 42: 10953

13a Li B, Li Y, Yu L, Wu X, Wei W. Tetrahedron 2017; 73: 2760
13b Taneja N, Peddinti RK. Eur. J. Org. Chem. 2017; 5306

14a Liu T, Zhou M, Yuan T, Fu B, Wang X, Peng F, Shao Z. Adv. Synth. Catal. 2017; 359: 89
14b Liu T, Liu J, He C, Cheng F. Chin. J. Org. Chem. 2017; 37: 2609
14c Liu T, Liu J, Xia S, Meng J, Shen X, Zhu X, Chen W, Sun C, Cheng F. ACS Omega 2018; 3: 1409

15 Santos MM. M, Moreira R. Mini-Rev. Med. Chem. 2007; 7: 1040
16 CCDC 1862387 (3aa) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
17 Wang B, Tang L, Liu L, Li Y, Yang Y, Wang Z. Green Chem. 2017; 19: 5794

18a Hashimoto T, Nakatsu H, Takiguchi Y, Maruoka K. J. Am. Chem. Soc. 2013; 135: 16010
18b Liu L, Chen K, Wu W.-Z, Wang P.-F, Song H.-Y, Sun H, Wen X, Xu Q.-L. Org. Lett. 2017; 19: 3823

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