Cobalt(III)-Catalyzed 1,4-Addition of C(sp3)–H Bonds to 
Maleimides

Xiang-Xiang Chen; Jiang-Tao Ren; Jing-Lei Xu; Hu Xie; Wei Sun; Ya-Min Li; Meng Sun

doi:10.1055/s-0037-1609847

Synlett, Table of Contents

Synlett 2018; 29(12): 1601-1606
DOI: 10.1055/s-0037-1609847

letter

Cobalt(III)-Catalyzed 1,4-Addition of C(sp³)–H Bonds to Maleimides

Authors

Xiang-Xiang Chen ◇
Jiang-Tao Ren ◇
Jing-Lei Xu
Hu Xie
Wei Sun
Ya-Min Li

^bFaculty of Life Science and Technology, Kunming University of Science and Technology, 727 Jingming Nanlu, Kunming 650500, P. R. of China
Meng Sun*

^aKey Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China Email: sunmeng@nwu.edu.cn

Abstract

All articles of this category

^◇ These authors contributed equally to this work.

Abstract

Quinolines and succinimides play a crucial role in many pharmaceutical and natural products. Although sp² C–H bond addition reactions have been extensively investigated, Co(III)-catalyzed sp³ C–H bond 1,4-addition reactions are relatively unexplored. In this manuscript, an efficient and atom-economic protocol for alkylation reactions of 8-methylquinolines with maleimides is presented. The reaction exhibits exceptional reactivity, satisfactory yields, excellent chemo- and regioselectivity, and tolerates a variety of functional groups.

Key words

cobalt - 1,4-addition reactions - alkylation - C–H functionalization - 8-methylquinolines

Full Text

References

References

For selected reviews, see:

1a Dyker G. Handbook of C–H Transformations: Applications in Organic Synthesis. Wiley-VCH; Weinheim: 2005
1b Activation and Functionalization of C–H Bonds . Goldberg KI. Goldman AS. ACS Symposium Series 885; Washington: 2004
1c Giri R. Shi B.-F. Engle KM. Maugel N. Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
1d Yu J.-Q. Shi Z.-J. C–H Activation . Springer; Berlin: 2010
1e Lyons TW. Sanford MS. Chem. Rev. 2010; 110: 1147
1f Colby DA. Bergman RG. Ellman JA. Chem. Rev. 2010; 110: 624
1g Colby DA. Tsai AS. Bergman RG. Ellman JA. Acc. Chem. Res. 2012; 45: 814
1h Song G. Li X. Acc. Chem. Res. 2015; 48: 1007
1i Ye B. Cramer N. Acc. Chem. Res. 2015; 48: 1308
1j He G. Wang B. Nack WA. Chen G. Acc. Chem. Res. 2016; 49: 635

2a Murai S. Kakiuchi F. Sekine S. Tanaka Y. Kamatani A. Sonoda M. Chatani N. Nature 1993; 366: 529
2b Leow D. Li G. Mei T.-S. Yu J.-Q. Nature 2012; 486: 518
2c Hennessy ET. Betley TA. Science 2013; 340: 591
2d McNally A. Haffemayer B. Collins BS. L. Gaunt MJ. Nature 2014; 510: 129
2e Tang R.-Y. Li Gang. Yu J.-Q. 2014; 507: 215
2f Sharma A. Hartwig JF. Nature 2015; 517: 600
2g Topczewski JJ. Cabrera PJ. Saper NI. Sanford MS. Nature 2016; 531: 220
2h Chu JC. K. Rovis T. Nature 2016; 539: 272
2i Le C. Liang Y. Evans RW. Li X. MacMillan DW. C. Nature 2017; 547: 79

For selected reviews on sp³ C−H bond activation see:

3a Jazzar R. Hitce J. Renaudat A. Sofack-Kreutzer J. Baudoin O. Chem. Eur. J. 2010; 16: 2654
3b Li H. Li B.-J. Shi Z.-J. Catal. Sci. Technol. 2011; 1: 191
3c Hartwig JF. Chem. Soc. Rev. 2011; 40: 1992
3d Li B.-J. Shi Z.-J. Chem. Soc. Rev. 2012; 41: 5588
3e Rouquet G. Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
3f Dastbaravardeh N. Christakakou M. Haider M. Schnurch M. Synthesis 2014; 46: 1421
3g Vanjari R. Singh KN. Chem. Soc. Rev. 2015; 44: 8062
3h Hartwig JF. J. Am. Chem. Soc. 2016; 138: 2

For selected reports on Pd-catalyzed sp³ C−H activation, see:

4a Shabashov D. Daugulis O. Org. Lett. 2005; 7: 3657
4b Kalyani D. Deprez NR. Desai LV. Sanford MS. J. Am. Chem. Soc. 2005; 127: 7330
4c Chen X. Goodhue CE. Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 12634
4d Thu H.-Y. Yu W.-Y. Che C.-M. J. Am. Chem. Soc. 2006; 128: 9048
4e Yu W.-Y. Sit WN. Lai K.-M. Zhou Z.-Y. Chan AS. C. J. Am. Chem. Soc. 2008; 130: 3304
4f Zhang J. Khaskin E. Anderson NP. Zavalij PY. Vedernikov AN. Chem. Commun. 2008; 3625
4g Iglesias A. Alvarez R. de Lera AR. Muniz K. Angew. Chem. Int. Ed. 2012; 51: 2225
4h Stowers KJ. Kubota A. Sanford MS. Chem. Sci. 2012; 3: 3192
4i Gulia N. Daugulis O. Angew. Chem. Int. Ed. 2017; 56: 3630

For selected reports on Rh(III)-catalyzed sp³ C−H activation, see:

5a Liu B. Zhou T. Li B. Xu S. Song H. Wang B. Angew. Chem. Int. Ed. 2014; 53: 4191
5b Wang X. Yu D.-G. Glorius F. Angew. Chem. Int. Ed. 2015; 54: 10280
5c Huang X. Wang Y. Lan J. You J. Angew. Chem. Int. Ed. 2015; 54: 9404
5d Wang H. Tang G. Li X. Angew. Chem. Int. Ed. 2015; 54: 13049
5e Zhou B. Chen Z. Yang Y. Ai W. Tang H. Wu Y. Zhu W. Li Y. Angew. Chem. Int. Ed. 2015; 54: 12121
5f Yu S. Tang G. Li Y. Zhou X. Lan Y. Li X. Angew. Chem. Int. Ed. 2016; 55: 8696
5g Tang C. Zou M. Liu J. Wen X. Sun X. Zhang Y. Jiao N. Chem. Eur. J. 2016; 22: 11165
5h Hou W. Yang Y. Wu Y. Feng H. Li Y. Zhou B. Chem. Commun. 2016; 52: 9672
5i Wippich J. Truchan N. Bach T. Adv. Synth. Catal. 2016; 358: 2083
5j Hu X.-H. Yang X.-F. Loh T.-P. ACS Catal. 2016; 6: 5930
5k Kim S. Han S. Park J. Sharma S. Mishra NK. Oh HJ. Kwak H. Kim IS. Chem. Commun. 2017; 53: 3006
5l Yuan C. Tu G. Zhao Y. Org. Lett. 2017; 19: 356

For selected reports on Ir(III)-catalyzed sp³ C−H activation, see:

6a Kang T. Kim H. Kim JG. Chang S. Chem. Commun. 2014; 50: 12073
6b Kang T. Kim Y. Lee D. Wang Z. Chang S. J. Am. Chem. Soc. 2014; 136: 4141
6c Gao P. Guo W. Xue J. Zhao Y. Yuan Y. Xia Y. Shi Z. J. Am. Chem. Soc. 2015; 137: 12231
6d Kim H. Park G. Park J. Chang S. ACS Catal. 2016; 6: 5922

For selected reports on Ru-catalyzed sp³ C−H activation, see:

7a Liu B. Li B. Wang B. Chem. Commun. 2015; 51: 16334
7b Murugesh V. Bruneau C. Achard M. Sahoo AR. Sharma GV. M. Suresh S. Chem. Commun. 2017; 53: 10448

For recent reviews, see:

8a Pellissier H. Clavier H. Chem. Rev. 2014; 114: 2775
8b Chirik PJ. Acc. Chem. Res. 2015; 48: 1687
8c Gandeepan P. Cheng C.-H. Acc. Chem. Res. 2015; 48: 1194
8d Yoshikai N. ChemCatChem 2015; 7: 732
8e Roese P. Hilt G. Synthesis 2016; 48: 463
8f Wei D. Zhu X. Niu J.-L. Song M.-P. ChemCatChem 2016; 8: 1242
8g Moselage M. Li J. Ackermann L. ACS Catal. 2016; 6: 498
8h Yoshino T. Matsunaga S. Adv. Synth. Catal. 2017; 359: 1245
8i Usman M. Ren Z.-H. Wang Y.-Y. Guan Z.-H. Synthesis 2017; 49: 1419
8j Wang S. Chen S.-Y. Yu X.-Q. Chem. Commun. 2017; 53: 3165

For selected reports on cobalt(III) catalyzed sp³ C−H activation, see:

9a Sen M. Emayavaramban B. Barsu N. Premkumar JR. Sundararaju B. ACS Catal. 2016; 6: 2792
9b Barsu N. Rahman MA. Sen M. Sundararaju B. Chem. Eur. J. 2016; 22: 9135
9c Mita T. Hanagata S. Michigami K. Sato Y. Org. Lett. 2017; 19: 5876
9d Zhou Y. Tang Z. Song Q. Chem. Commun. 2017; 53: 8972
9e Tan PW. Mak AM. Sullivan MB. Dixon DJ. Seayad J. Angew. Chem. Int. Ed. 2017; 56: 16550
9f Yan S.-Y. Ling P.-X. Shi B.-F. Adv. Synth. Catal. 2017; 359: 2912
9g Zhang Z.-Z. Han Y.-Q. Zhan B.-B. Wang S. Shi B.-F. Angew. Chem. Int. Ed. 2017; 56: 13145
9h Wu X. Yang K. Zhao Y. Sun H. Li G. Ge H. Nat. Commun. 2015; 6: 6462
9i Zhang J. Chen H. Lin C. Liu Z. Wang C. Zhang Y. J. Am. Chem. Soc. 2015; 137: 12990
9j Barsu N. Bolli SK. Sundararaju B. Chem. Sci. 2017; 8: 2431
9k Williamson P. Galván A. Gaunt MJ. Chem. Sci. 2017; 8: 2588

Rh-catalyzed:

10a Han SH. Kim S. De U. Mishra NK. Park J. Sharma S. Kwak JH. Han S. Kim HS. Kim IS. J. Org. Chem. 2016; 81: 12416
10b Sharma S. Han SH. Oh Y. Mishra NK. Lee SH. Oh JS. Kim IS. Org. Lett. 2016; 18: 2568
10c Han S. Park J. Kim S. Lee SH. Sharma S. Mishra NK. Jung YH. Kim IS. Org. Lett. 2016; 18: 4666
10d Sharma S. Han SH. Jo H. Han S. Mishra NK. Choi M. Jeong T. Park J. Kim IS. Eur. J. Org. Chem. 2016; 3611

Ru-catalyzed:

10e Keshri P. Bettadapur KR. Lanke V. Prabhu KR. J. Org. Chem. 2016; 81: 6056
10f Bettadapur KR. Lanke V. Prabhu KR. Org. Lett. 2015; 17: 4658
10g Lanke V. Bettadapur KR. Prabhu KR. Org. Lett. 2015; 17: 4662

Cu-catalyzed:

10h Miura W. Hirano K. Miura M. Org. Lett. 2015; 17: 4034

Co(III)-catalyzed:

10i Yu W. Zhang W. Liu Y. Liu Z. Zhang Y. Org. Chem. Front. 2017; 4: 77
10j Zhang Z. Han S. Tang M. Ackermann L. Li J. Org. Lett. 2017; 19: 3315
10k Muniraj N. Prabhu KR. J. Org. Chem. 2017; 82: 6913
10l Zell D. Bursch M. Muller V. Grimme S. Ackermann L. Angew. Chem. Int. Ed. 2017; 56: 10378
10m Muniraj N. Prabhu KR. ACS Omega 2017; 2: 4470
10n Barsu N. Emayavaramban B. Sundararaju B. Eur. J. Org. Chem. 2017; 4370
10o Chen X. Ren J. Xie H. Sun W. Sun M. Wu B. Org. Chem. Front. 2018; 5: 184
10p Liu S.-L. Li Y. Guo J.-R. Yang G.-C. Li X.-H. Gong J.-F. Song M.-P. Org. Lett. 2017; 19: 4042
10q Zhan B.-B. Li Y. Xu J.-W. Nie X.-L. Fan J. Jin L. Shi B.-F. Angew. Chem. Int. Ed. 2018; 57: 5858

11a Crider AM. Kolczynski TM. Yates KM. J. Med. Chem. 1980; 23: 324
11b Isaka M. Rugseree N. Maithip P. Kongsaeree P. Prabpai S. Thebtaranonth Y. Tetrahedron 2005; 61: 5577
11c Uddin J. Ueda K. Siwu ER. O. Kita M. Uemura D. Bioorg. Med. Chem. 2006; 14: 6954
11d Cho H. Engers D. Venable D. Niswender C. Lindsley C. Conn P. Emmitte K. Rodriguez A. ACS Chem. Neurosci. 2014; 5: 597
11e Cheng C.-F. Lai Z.-C. Lee Y.-J. Tetrahedron 2008; 64: 4347
11f Rankin GO. Cressey-Veneziano K. Wang R.-T. Brown PI. J. Appl. Toxicol. 1986; 6: 349
11g Deeks ED. Drugs 2015; 75: 1393
11h Shoji A. Kuwahara M. Ozaki H. Sawai H. J. Am. Chem. Soc. 2007; 129: 1456
11i Luzzio FA. Duveau DY. Lepper ER. Figg WD. J. Org. Chem. 2005; 70: 10117
11j Ishiyama T. Tokuda K. Ishibashi T. Ito A. Toma S. Ohno Y. Eur. J. Pharmacol. 2007; 572: 160

12a Zhang L. Tan Y. Wang N.-X. Wu Q.-Y. Xi Z. Yang G.-F. Bioorg. Med. Chem. 2010; 18: 7948
12b Ibnusaud I. Thomas G. Tetrahedron Lett. 2003; 44: 1247

13 Representative Procedure for 1,4-Addition of C(sp³)−H Bonds to Maleimides A mixture of 8-methylquionoline (28.6 mg, 0.2 mmol, 1.0 equiv), N-methylmaleimide (44.4 mg, 0.4 mmol, 2.0 equiv), [Cp*Co(CO)I₂] (4.8 mg, 0.01 mmol, 5 mol%), AgOTf (7.7 mg, 0.03 mmol, 15 mol%), and Zn(OAc)₂ (11.0 mg, 0.06 mmol, 30 mol%) in HFIP (1.0 mL) was stirred under argon at 100 °C for 24 h. After cooling to room temperature, the solvent was removed under reduced pressure. The contents were subjected to flash chromatography (petrol ether/EtOAc 2:1) to give the product as white solid (46.7 mg, 0.184 mmol, 92%). 1-Methyl-3-(quinolin-8-ylmethyl)pyrrolidine-2,5-dione (3aa) Yellow solid. ¹H NMR (400 MHz, CDCl₃): δ = 8.90 (dd, J = 1.6, 4.0 Hz, 1 H), 8.14 (dd, J = 1.6, 8.0 Hz, 1 H), 7.73 (dd, J = 1.2, 8.0 Hz, 1 H), 7.57 (d, J = 4.0 Hz, 1 H), 7.46 (t, J = 8.0 Hz, 1 H), 7.41 (dd, J = 4.0, 8.0 Hz, 1 H), 3.97 (dd, J = 8.0, 16.0 Hz, 1 H), 3.54−3.47 (m, 1 H), 3.42−3.36 (m, 1 H), 2.97 (s, 3 H), 2.64 (dd, J = 4.0, 18.4 Hz, 1 H), 2.54 (dd, J = 8.8, 18.4 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 179.84, 176.98, 149.63, 146.84, 136.51, 136.38, 129.99, 128.47, 127.27, 126.25, 121.17, 41.31, 33.73, 32.21, 24.71. HRMS (ESI): m/z [M + Na]⁺ calcd for C₁₅H₁₄N₂O₂Na⁺: 277.0953; found: 277.0987.
14 The 1,4-addition product with unprotected maleimide was isolated in no more than 10% yield, accompanied with recovered starting materials.
15 Kim KO. Choi T.-L. Macromolecules 2013; 46: 5905

Supplementary Material

Supporting Information (PDF)

Cobalt(III)-Catalyzed 1,4-Addition of C(sp3)–H Bonds to Maleimides

Authors

Cobalt(III)-Catalyzed 1,4-Addition of C(sp³)–H Bonds to Maleimides