Reassembly of Unsaturated C–C Bonds by a Cutting/Insertion Cascade

Ying Xu; Ling Li; Min Zhao; Yaojia Jiang

doi:10.1055/a-1983-1750

Synlett, Table of Contents

Synlett 2023; 34(04): 293-300
DOI: 10.1055/a-1983-1750

synpacts

Reassembly of Unsaturated C–C Bonds by a Cutting/Insertion Cascade

Ying Xu

^aLaboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, P. R. of China

,

Ling Li

^aLaboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, P. R. of China

,

Min Zhao

^aLaboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, P. R. of China

,

Yaojia Jiang∗

^aLaboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, P. R. of China

^bInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, P. R. of China

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Abstract

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Abstract

The reassembly of unsaturated C–C bonds has attracted widespread attention from synthetic chemists due to its advantages of unique reactivity, easy handling, and high atom and step economies. We recently explored a cutting/insertion cascade as a means of introducing a new C₁ source and constructing functionalized 1,4-keto aldehyde and 2H-furan derivatives through cyclopropanation of enamines with various carbene precursors and subsequent ring-opening reactions in situ. Aminocyclopropanes are believed to be involved as key intermediates in these transformations. This Synpacts article outlines our recent contributions to this increasingly important research area.

1 Introduction

2 Cleavage of Enamine C=C Double Bonds and Hydrolysis to 1,4-Keto Aldehydes

3 Cleavage of Enamine C=C Double Bonds and Cyclization to 2H-Furans

4 Cleavage of Ynone/Ynoate C≡C Triple Bonds

5 Conclusion

Key words

carbenes - enamines - cascade reaction - cyclopropanes - keto aldehydes - furans

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References

References

1a Xue Y, Dong G. Acc. Chem. Res. 2022; 55: 2341
1b Xu Y, Dong G. Chem 2020; 6: 10
1c Xia Y, Lu G, Liu P, Dong G. Nature 2016; 539: 546
1d Deng L, Dong G. Trends Chem. 2020; 2: 183
1e Long Y, Su Z, Zheng Y, He S, Zhong J, Xiang H, Zhou X. ACS Catal. 2020; 10: 3398
1f He T, Chen D, Qian S, Zheng Y, Huang S. Org. Lett. 2021; 23: 6525

2a Crabtree RH. Chem. Rev. 1985; 85: 245
2b Webster DE. Adv. Organomet. Chem. 1977; 15: 147

3a Miyamoto K, Tada N, Ochiai M. J. Am. Chem. Soc. 2007; 129: 2772
3b Vougioukalakis GC, Grubbs RH. Chem. Rev. 2010; 110: 1746
3c Wang T, Jiao N. J. Am. Chem. Soc. 2013; 135: 11692
3d Ludwig JB, Zimmerman PM, Gianino JB, Schindler CS. Nature 2016; 533: 374
3e Griffith AK, Vanos CM, Lambert TH. J. Am. Chem. Soc. 2012; 134: 18581

4a Calderon N. Acc. Chem. Res. 1972; 5: 127
4b Hong SH, Sander DP, Lee CW, Grubbs RH. J. Am. Chem. Soc. 2005; 127: 17160
4c Rosebrugh LE, Herbert MB, Marx VM, Keitz BK, Grubbs RH. J. Am. Chem. Soc. 2013; 135: 1276
4d Ogba OM, Warner NC, O’Leary DJ, Grubbs RH. Chem. Soc. Rev. 2018; 47: 4510
4e Turczel G, Kovács E, Merza G, Coish P, Anastas PT, Tuba R. ACS Sustainable Chem. Eng. 2019; 7: 33

5a Chauvin Y. Angew. Chem. Int. Ed. 2006; 45: 3740
5b Schrock RR. Angew. Chem. Int. Ed. 2006; 45: 3748
5c Grubbs RH. Angew. Chem. Int. Ed. 2006; 45: 3760

6a Theunissen C, Ashley MA, Rovis T. J. Am. Chem. Soc. 2019; 141: 6791
6b Ruffoni A, Hampton C, Simonetti M, Leonori D. Nature 2022; 610: 81
6c Wise DE, Gogarnoiu ES, Duke AD, Paolillo JM, Vacala TL, Hussain WA, Parasram M. J. Am. Chem. Soc. 2022; 144: 15437
6d Patra T, Wirth T. Angew. Chem. Int. Ed. 2022; 61: e202213772

7a Gómez-Gallego M, Mancheño MJ, Sierra MA. Acc. Chem. Res. 2005; 38: 44
7b Jiang Y, Sun R, Tang X.-Y, Shi M. Chem. Eur. J. 2016; 22: 17910
7c Zhou S, Li J, Schlangen M, Schwarz H. Acc. Chem. Res. 2016; 49: 494

8a Li C, Zeng Y, Zhang H, Feng J, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2010; 49: 6413
8b Zhou B, Chen Z, Yang X, Ai W, Tang H, Wu Y, Zhu W, Li Y. Angew. Chem. Int. Ed. 2015; 54: 12121
8c Zheng H, Doyle MP. Angew. Chem. Int. Ed. 2019; 58: 12502
8d Wang X, Abrahams QM, Zavalij PY, Doyle MP. Angew. Chem. Int. Ed. 2012; 51: 5907
8e Jana S, Pei C, Empel C, Koenigs RM. Angew. Chem. Int. Ed. 2021; 60: 13271

9a Mata S, López LA, Vicente R. Angew. Chem. Int. Ed. 2017; 56: 7930
9b Cai B.-G, Chen Z.-L, Xu G.-Y, Xuan J, Xiao W.-J. Org. Lett. 2019; 21: 4234

10a Miege F, Meyer C, Cossy J. Angew. Chem. Int. Ed. 2011; 50: 5932
10b Jurberg ID, Davies HM. L. Chem. Sci. 2018; 9: 5112
10c Yang Z, Stivanin ML, Jurberg ID, Koenigs RM. Chem. Soc. Rev. 2020; 49: 6833
10d Klöpfer V, Eckl R, Floß J, Roth PM. C, Reiser O, Barham JP. Green Chem. 2021; 23: 6366

11a Masarwa A, Stanger A, Marek I. Angew. Chem. Int. Ed. 2007; 46: 8039
11b Xiao T, Mei M, He Y, Zhou L. Chem. Commun. 2018; 54: 8865
11c Zhou Y, Trewyn BG, Angelici RJ, Woo LK. J. Am. Chem. Soc. 2009; 131: 11734

12a Reisman SE, Nani RR, Levin S. Synlett 2011; 2437
12b Duchemina C, Cramer N. Chem. Sci. 2019; 10: 2773
12c Chauhan J, Ravva MK, Gremaud L, Sen S. Org. Lett. 2020; 22: 4537
12d Sharland JC, Dunstan D, Majumdar D, Gao JH, Tan K, Malik HA, Davies HM. L. ACS Catal. 2022; 12: 12530

13a Li M, Sun Y, Xie Y, Yu Y, Huang F, Huang H. Chem. Commun. 2020; 56: 11050
13b Bagle PN, Mane MV, Sancheti SP, Gade AB, Shaikh SR, Baik M.-H, Patil NT. Org. Lett. 2018; 21: 335
13c Li W, Yang Y, Tang Z, Yu X, Lin J, Jin Y. J. Org. Chem. 2022; 87: 13352

14a Huang W, Keess S, Molander GA. Chem. Sci. 2022; 13: 11936
14b Zhang Y, Niu Y, Guo Y, Wang J, Zhang Y, Liu S, Shen X. Angew. Chem. Int. Ed. 2022; 61: e202212201
14c Yu X.-Y, Chen J.-R, Xiao W.-J. Chem. Rev. 2021; 121: 506

15a Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
15b Skubi KL, Blum TR, Yoon TP. Chem. Rev. 2016; 116: 10035
15c Chen Y, Lu L.-Q, Yu D.-G, Zhu C.-J, Xiao W.-J. Sci. China Chem. 2019; 62: 24

16a Jun C.-H. Chem. Soc. Rev. 2004; 33: 610
16b Chatani N, Tobisu M. Chem. Soc. Rev. 2008; 37: 300
16c Kolle S, Batra S. Org. Biomol. Chem. 2016; 14: 11048

17a Yorimitsu H, Oshima K. Bull. Chem. Soc. Jpn. 2009; 82: 778
17b Nogi K, Yorimitsu H. Chem. Rev. 2021; 121: 345

18 O’Brien M, Baxendale IR, Ley SV. Org. Lett. 2010; 12: 1596

19a Grubbs RH, Miller SJ, Fu GC. Acc. Chem. Res. 1995; 28: 446
19b Hoveyda AH, Zhugralin AR. Nature 2007; 450: 243
19c Bidange J, Fischmeister C, Bruneau C. Chem. Eur. J. 2016; 22: 12226

20a Filippov IP, Titov GD, Rostovskii NV. Synthesis 2020; 52: 3564
20b Yadagiri D, Rivas M, Gevorgyan V. J. Org. Chem. 2020; 85: 11030
20c Kim JH, Gensch T, Zhao DB, Stegemann L, Strassert CA, Glorius F. Angew. Chem. Int. Ed. 2015; 54: 10975

21a Furniel LG, Echemendía R, Burtoloso AC. B. Chem. Sci. 2021; 12: 7453
21b Wu X, Sun S, Yu J.-T, Cheng J. Synlett 2019; 30: 21
21c Barday M, Janot C, Halcovitch NR, Muir J, Aïssa C. Angew. Chem. Int. Ed. 2017; 56: 13117
21d Leveille AN, Echemendía R, Mattson AE, Burtoloso AC. B. Org. Lett. 2021; 23: 9446

22a Zhang Y, Zhang Y, Ye C, Qi X, Wu L.-Z, Shen X. Nat. Commun. 2022; 13: 6111
22b Ye J.-H, Quach L, Paulisch T, Glorius F. J. Am. Chem. Soc. 2019; 141: 16227
22c Sakurai S, Inagaki T, Kodama T, Yamanaka M, Tobisu M. J. Am. Chem. Soc. 2022; 144: 1099
22d Zhang Y, Zhou G, Gong X, Guo Z, Qi X, Shen X. Angew. Chem. Int. Ed. 2022; 61: e202202175
22e Stuckhardt C, Wissing M, Studer A. Angew. Chem. Int. Ed. 2021; 60: 18605

23a Dattatri Dattatri, Singam MK. R, Nanuboluc JB. N, Reddy MS. Org. Biomol. Chem. 2022; 20: 6363
23b Luo K, Mao S, He K, Yu X, Pan J, Lin J, Shao Z, Jin Y. ACS Catal. 2020; 10: 3733

24a DeMartino MP, Chen K, Baran PS. J. Am. Chem. Soc. 2008; 130: 11546
24b Davies SS, Amarnath V, Brame CJ, Boutaud O, Roberts LJ. II. Nat. Protoc. 2007; 2: 2079

25 Ni M, Zhang J, Liang X, Jiang Y, Loh T.-P. Chem. Commun. 2017; 53: 12286
26 Chen J, Guo P, Zhang J, Rong J, Sun W, Jiang Y, Loh T.-P. Angew. Chem. Int. Ed. 2019; 58: 12674

27a Ross RJ, Jeyaseelan R, Lautens M. Org. Lett. 2020; 22: 4838
27b Guo P, Sun W, Liu Y, Li Y.-X, Loh T.-P, Jiang Y. Org. Lett. 2020; 22: 5978

28 Chen J, Han J, Wu T, Zhang J, Li M, Xu Y, Zhang J, Jiao Y, Yang Y, Jiang Y. Org. Chem. Front. 2022; 9: 1820

29a Delcamp JH, Gormisky PE, White MC. J. Am. Chem. Soc. 2013; 135: 8460
29b Harned AM, Volp KA. Nat. Prod. Rep. 2011; 28: 1790
29c Zorn H, Langhoff S, Scheibner M, Nimtz M, Berger RG. Biol. Chem. 2003; 384: 1049

30 Diver ST. Giessert A. J. Chem. Rev. 2004; 104: 1317
31 Shang X, Liu Z.-Q. Chem. Soc. Rev. 2013; 42: 3253
32 Jiang C, Wu J, Han J, Chen K, Qian Y, Zhang Z, Jiang Y. Chem. Commun. 2021; 57: 5710

33a Li X, Hou Y, Meng X, Ge C, Ma H, Li J, Fang J. Angew. Chem. Int. Ed. 2018; 57: 6141
33b Hansen MR, Hurley LH. Acc. Chem. Res. 1996; 29: 249
33c Li D.-F, Hu P.-P, Liu M.-S, Kong X.-L, Zhang J.-C, Hider RC, Zhou T. J. Agric. Food Chem. 2013; 61: 6597
33d Caturla F, Jiménez J.-M, Godessart N, Amat M, Cárdenas A, Soca L, Beleta J, Ryder H, Crespo MI. J. Med. Chem. 2004; 47: 3874
33e Puerta DT, Mongan J, Tran BL, McCammon JA, Cohen SM. J. Am. Chem. Soc. 2005; 127: 14148
33f Carnaghan RB. A, Hartley RD, O’Kelly J. Nature 1963; 200: 1101

34a Evans DA, Sweeney ZK, Rovis T, Tedrow JS. J. Am. Chem. Soc. 2001; 123: 12095
34b Zhou J.-L, Liang Y, Deng C, Zhou H, Wang Z, Sun X.-L, Zheng J.-C, Yu Z.-X, Tang Y. Angew. Chem. Int. Ed. 2011; 50: 7874

35a Dou G.-Y, Jiang Y.-Y, Xu K, Zeng C.-C. Org. Chem. Front. 2019; 6: 2392
35b Proctor RS. J, Phipps RJ. Angew. Chem. Int. Ed. 2019; 58: 13666
35c O’Brien AG, Maruyama A, Inokuma Y, Fujita M, Baran PS, Blackmond DG. Angew. Chem. Int. Ed. 2014; 53: 11868
35d Hamadi NB. J. Fluorine Chem. 2015; 170: 47

36a Furuya T, Kamlet AS, Ritter T. Nature 2011; 473: 470
36b Prakash GK. S, Jog PV, Batamack PT. D, Olah GA. Science 2012; 338: 1298
36c Liang T, Neumann CN, Ritter T. Angew. Chem. Int. Ed. 2013; 52: 8214

37 Liang X, Guo P, Yang W, Jiang C, Sun W, Loh T.-P, Jiang Y. Chem. Commun. 2020; 56: 2043

38a Xie Y, Chi H.-W, Guan A.-Y, Liu C.-L, Ma H.-J, Cui D.-L. J. Agric. Food Chem. 2014; 62: 12491
38b Chen J, Yi C, Wang S, Wu S, Li S, Hu D, Song B. Bioorg. Med. Chem. Lett. 2019; 29: 1203
38c Cai M, Li Z, Fan F, Huang Q, Shao X, Song G. J. Agric. Food Chem. 2010; 58: 2624
38d Nugent BM, Buysse AM, Loso MR, Babcock JM, Johnson TC, Oliver MP, Martin TP, Ober MS, Breaux N, Robinson A, Adelfinskaya Y. Pest Manage. Sci. 2015; 71: 928

39a Ferraris D, Duvall B, Delahanty G, Mistry B, Alt J, Rojas C, Rowbottom C, Sanders K, Schuck E, Huang K.-C, Redkar S, Slusher BB, Tsukamoto T. J. Med. Chem. 2014; 57: 2582
39b Cacciamani T, Vita A, Cristalli G, Vincenzetti S, Natalini P, Ruggieri S, Amici A, Magni G. Arch. Biochem. Biophys. 1991; 290: 285

40 Wang F, Fu R, Chen J, Rong J, Wang E, Zhang J, Zhang Z, Jiang Y. Chem. Commun. 2022; 58: 3477
41 Ying JB, Liu T, Liu Y, Wan J.-P. Org. Lett. 2022; 24: 2404
42 Sheng H, Chen Z, Li X, Su J, Song Q. Org. Chem. Front. 2022; 9: 3000
43 Chen Z, Xie X, Chen W, Luo N, Li X, Yu F, Huang J. Org. Biomol. Chem. 2022; 20: 8037
44 Rong J, Li H, Fu R, Sun W, Loh T.-P, Jiang Y. ACS Catal. 2020; 10: 3664