Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Iso­cyanide as CO Equivalent Leading to 1,2-Diketones

Zhiyuan Tu; Jianan Zhan; Shengyong You; Mingzhong Cai

doi:10.1055/s-0040-1720121

Synthesis, Table of Contents

Synthesis 2024; 56(13): 2015-2024
DOI: 10.1055/s-0040-1720121

paper

Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Isocyanide as CO Equivalent Leading to 1,2-Diketones

Authors

Zhiyuan Tu

^aKey Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China
Jianan Zhan

^aKey Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China
Shengyong You∗

^bInstitute of Applied Chemistry, Jiangxi Academy of Sciences, Nanchang 330029, P. R. of China
Mingzhong Cai ∗

^aKey Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China

Abstract

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Abstract

An efficient heterogeneous palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum compounds has been developed using tert-butyl isocyanide as CO equivalent. The carbonylation reaction proceeds smoothly in toluene with KO^tBu as a base at 100 °C by using 10 mol% of an SBA-15-anchored bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] as the catalyst and provides a general and practical approach for the assembly of 1,2-diketones in good to excellent yields. This heterogenized palladium catalyst can be readily separated and recovered via a simple centrifugation process and reused for more than seven cycles with almost consistent catalytic efficiency.

Key words

palladium - carbonylative coupling - organoaluminum reagents - 1,2-diketones - heterogeneous catalysis

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References

References

1a Fan T.-Y, Wu W.-Y, Yu S.-P, Zhong Y, Zhao C, Chen M, Li H.-M, Li N.-G, Chen Z, Chen S, Sun Z.-H, Duan J.-A, Shi Z.-H. Bioorg. Med. Chem. Lett. 2019; 29: 126772
1b Kucukkilinc TT, Yanghagh KS, Ayazgok B, Roknipour MA, Moghadam FH, Moradi A, Emami S, Amini M, Irannejad H. Med. Chem. Res. 2017; 26: 3057
1c Cumming JN, Smith EM, Wang L, Misiaszek J, Durkin J, Pan J, Iserloh U, Wu Y, Zhu Z, Strickland C, Voigt J, Chen X, Kennedy ME, Kuvelkar R, Hyde LA, Cox K, Favreau L, Czarniecki MF, Greenlee WJ, McKittrick BA, Parker EM, Stamford AW. Bioorg. Med. Chem. Lett. 2012; 22: 2444
1d Al-kahraman YM. S. A, Yasinzai M, Singh GS. Arch. Pharmacal. Res. 2012; 35: 1009

2a Yan Q, Ma X, Banwell MG, Ward JS. J. Nat. Prod. 2017; 80: 3305
2b Luan Y, Wei H, Zhang Z, Che Q, Liu Y, Zhu T, Mandi A, Kurtan T, Gu Q, Li D. J. Nat. Prod. 2014; 77: 1718
2c Shen Y, Feng Z.-M, Jiang J.-S, Yang Y.-N, Zhang P.-C. J. Nat. Prod. 2013; 76: 2337

3a Mousset C, Giraud A, Provot O, Hamze A, Bignon J, Liu J.-M, Thoret S, Dubois J, Brion J.-D, Alami M. Bioorg. Med. Chem. Lett. 2008; 18: 3266
3b Ganapaty S, Srilakshmi GV. K, Pannakal ST, Rahman H, Laatsch H, Brun R. Phytochemistry 2009; 70: 95

4a Hernandez-Cruz O, Zolotukhin MG, Fomine S, Alexandrova L, Aguilar-Lugo C, Ruiz-Trevino FA, Ramos-Ortiz G, Maldonado JL, Cadenas-Pliego G. Macromolecules 2015; 48: 1026
4b Mosnacek J, Weiss RG, Lukac I. Macromolecules 2002; 35: 3870
4c Huang S, Gao T, Bi A, Cao X, Feng B, Liu M, Du T, Feng X, Zeng W. Dyes Pigm. 2020; 172: 107830
4d Kawai S, Yamaguchi T, Kato T, Hatano S, Abe J. Dyes Pigm. 2012; 92: 872

5a Erker G, Czisch P, Schlund R, Angermund K, Kruger C. Angew. Chem., Int. Ed. Engl. 1986; 25: 364
5b Hofmann P, Frede M, Stauffert P, Lasser W, Thewalt U. Angew. Chem., Int. Ed. Engl. 1985; 24: 712
5c Spikes GH, Sproules S, Bill E, Weyhermuller T, Wieghardt K. Inorg. Chem. 2008; 47: 10935
5d van Vezen NJ. C, Harder S. Organometallics 2018; 37: 2263
5e Cesari C, Sambri I, Zacchini S, Zanotti V, Mazzoni R. Organometallics 2014; 33: 2814

6a Wang G, Wang J, He D, Li X, Li J, Peng Z. Bioorg. Med. Chem. Lett. 2016; 26: 2806
6b Scott JD, Li SW, Brunskill AP. J, Chen X, Cox K, Cumming JN, Forman M, Gilbert EJ, Hodgson RA, Hyde LA, Jiang Q, Iserloh U, Kazakevich I, Kuvelkar R, Mei H, Meredith J, Misiaszek J, Orth P, Rossiter LM, Slater M, Stone J, Strickland CO, Voigt JH, Wang G, Wang H, Wu Y, Greenlee WJ, Parker EM, Kennedy ME, Stamford AW. J. Med. Chem. 2016; 59: 10435
6c Hicks LD, Hyatt JL, Moak T, Edwards CC, Tsurkan L, Wierdl M, Ferreira AM, Wadkins RM, Potter PM. Bioorg. Med. Chem. 2007; 15: 3801

7a McKenna JM, Halley F, Souness JE, McLay IM, Pickett SD, Collis AJ, Page K, Ahmed I. J. Med. Chem. 2002; 45: 2173
7b Deng X, Mani NS. Org. Lett. 2006; 8: 269
7c Wolkenberg SE, Wisnoski DD, Leister WH, Wang Y, Zhao Z, Lindsley CW. Org. Lett. 2004; 6: 1453
7d Zhao Z, Wisnoski DD, Wolkenberg SE, Leister WH, Wang Y, Lindsley CW. Tetrahedron Lett. 2004; 45: 4873
7e Schmitt DC, Lam L, Johnson JS. Org. Lett. 2011; 13: 5136

8a Lee JC, Park H.-J, Park JY. Tetrahedron Lett. 2002; 43: 5661
8b Qi C, Jiang H, Huang L, Chen Z, Chen H. Synthesis 2011; 387
8c Su Y, Zhang L, Jiao N. Org. Lett. 2011; 13: 2168
8d Urgoitia G, SanMartin R, Herrero MT, Dominguez E. Green Chem. 2011; 13: 2161
8e Chang HS, Woo JC, Lee KM, Ko YK, Moon S.-S, Kim D.-W. Synth. Commun. 2002; 32: 31
8f Chen C.-T, Kao J.-Q, Salunke SB, Lin Y.-H. Org. Lett. 2011; 13: 26
8g Chebolu R, Bahuguna A, Sharma R, Mishra VK, Ravikumar PC. Chem. Commun. 2015; 51: 15438

9a Wang Z, Jiang H, Li X. J. Org. Chem. 2011; 76: 6958
9b Chen S, Liu Z, Shi E, Chen L, Wei W, Li H, Cheng Y, Wan X. Org. Lett. 2011; 13: 2274
9c Schmidt B, Krehl S, Hauke S. J. Org. Chem. 2013; 78: 5427
9d Su X, Sun X, Wu G, Jiao N. Angew. Chem. Int. Ed. 2013; 52: 9808
9e Song T, Ma Z, Ren P, Yuan Y, Xiao J, Yang Y. ACS Catal. 2020; 10: 4617

10a Gao A, Yang F, Li J, Wu Y. Tetrahedron 2012; 68: 4950
10b Xu YWan X. Tetrahedron Lett. 2013; 54: 642
10c Sawama Y, Takubo M, Mori S, Monguchi Y, Sajiki H. Eur. J. Org. Chem. 2011; 3361
10d Zhou J, Tao X.-Z, Dai J.-J, Li C.-G, Xu J, Xu H.-M, Xu H.-J. Chem. Commun. 2019; 55: 9208
10e Ynag W, Chen Y, Yao Y, Yang X, Lin Q, Yang D. J. Org. Chem. 2019; 84: 11080
10f Kim SW, Um T.-W, Shin S. J. Org. Chem. 2018; 83: 4703
10g Yuan L.-Z, Hamze A, Alami M, Provot O. Synthesis 2017; 49: 504
10h Xu C.-F, Xu M, Jia Y.-X, Li C.-Y. Org. Lett. 2011; 13: 1556
10i Dubovtsev AY, Shchebakov NV, Dar’in DV, Kukushkin VY. J. Org. Chem. 2020; 85: 745
10j Zhu X, Li P, Shi Q, Wang L. Green Chem. 2016; 18: 6373
10k Shen D, Wang H, Zheng Y, Zhu X, Gong P, Wang B, You J, Zhao Y, Chao M. J. Org. Chem. 2021; 86: 5354

11 Lv W.-X, Zeng Y.-F, Zhang S.-S, Li Q.-J, Wang H.-G. Org. Lett. 2015; 17: 2972

12a Min H, Palani T, Park K, Hwang J, Lee S. J. Org. Chem. 2014; 79: 6279
12b Chand S, Pandey AK, Singh R, Singh KN. J. Org. Chem. 2021; 86: 6486

13a Brennfuhrer H, Neumann H, Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114
13b Wu X.-F, Neumann H, Beller M. Chem. Soc. Rev. 2011; 40: 4986
13c Wu X.-F, Neumann H, Beller M. Chem. Rev. 2013; 113: 1
13d Wu X.-F, Neumann H, Beller M. ChemSusChem 2013; 6: 229

14a Vlaar T, Ruijter E, Maes BU. W, Orru RV. A. Angew. Chem. Int. Ed. 2013; 52: 7084
14b Boyarskiy VP, Bokach NA, Luzyanin KV, Kukushkin VY. Chem. Rev. 2015; 115: 2698
14c Wu L, Liu Q, Jackstell R, Beller M. Angew. Chem. Int. Ed. 2014; 53: 6310
14d Gautam P, Bhanage BM. Catal. Sci. Technol. 2015; 5: 4663

15a Tang T, Fei X.-D, Ge Z.-Y, Chen Z, Zhu Y.-M, Ji S.-J. J. Org. Chem. 2013; 78: 3170
15b Jiang X, Wang J.-M, Zhang Y, Chen Z, Zhu Y.-M, Ji S.-J. Org. Lett. 2014; 16: 3492
15c Zhang Y, Jiang X, Wang JM, Chen JL, Zhu YM. RSC Adv. 2015; 5: 17060
15d Chen ZB, Liu K, Zhang F.-L, Yuan Q, Zhu YM. Org. Biomol. Chem. 2017; 15: 8078
15e Jiang H, Liu B, Li Y, Wang A, Huang H. Org. Lett. 2011; 13: 1028
15f Zhu F, Li Y, Wang Z, Orru RV. A, Maes BU. W, Wu X.-F. Chem. Eur. J. 2016; 22: 7743

16a Ren S, Huang K, Liu J.-B, Zhang L, Hou M, Qiu G. Chin. Chem. Lett. 2022; 33: 4870
16b Chen D, Li J, Wang X, Shan Y, Huang K, Yan X, Qiu G. Org. Chem. Front. 2022; 9: 4209

17 Dechert-Schmitt A.-M, Garnsey MR, Wisniewska HM, Murray JI, Lee T, Kung DW, Sach N, Blackmond DG. ACS Catal. 2019; 9: 4508
18 Chen B, Wu X.-F. Org. Lett. 2020; 22: 636

19a Iwasawa Y. Tailored Metal Catalysts 1986
19b Dusi M, Mallat T, Baiker A. Catal. Rev.: Sci. Eng. 2000; 42: 213
19c Phan NT. S, Sluys MV. D, Jones CW. Adv. Synth. Catal. 2006; 348: 609
19d Gladysz JA. In Recoverable and Recyclable Catalysts . Benaglia M. John Wiley and Sons; Chichester: 2009: 1-14
19e Macquarrie D. In Heterogenized Homogeneous Catalysts for Fine Chemicals Production . Barbaro P, Liguori F. Springer; Berlin: 2010: 1-35

20a Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
20b Molnar A. Chem. Rev. 2011; 111: 2251

21a Zhao D, Feng J, Huo Q, Melosh N, Fredrickson GH, Chmelka BF, Stucky GD. Science 1998; 279: 548
21b Friedrich H, Sietsma JR. A, de Jongh PE, Verkleij AJ, de Jong KP. J. Am. Chem. Soc. 2007; 129: 10249

22 Baltes M, Cassiers K, Van Der Voort P, Weckhuysen BM, Schoonheydt RA, Vansant EF. J. Catal. 2001; 197: 160

23a Wu F, Feng Y, Jones CW. ACS Catal. 2014; 4: 1365
23b Rohani S, Ziarani GM, Badiei A, Ziarati A, Jafari M, Shayyesteh A. Appl. Organomet. Chem. 2018; 32: e4397
23c Nouri K, Hajjami M, Azadi G. Catal. Lett. 2018; 148: 671
23d Lai YT, Chen TC, Lan YK, Chen BS, You JH, Yang CM, Lai NC, Wu JH, Chen CS. ACS Catal. 2014; 4: 3824
23e Yang Y, Rioux RM. Chem. Commun. 2011; 47: 6557
23f Huo Y, Hu J, Lin S, Ju X, Wei Y, Huang Z, Hu Y, Tu Y. Appl. Organomet. Chem. 2019; 33: e4874
23g Zhao J, Yuan H, Qin X, Tian K, Liu Y, Wei C, Zhang Z, Zhou L, Fang S. Catal. Lett. 2020; 150: 2841
23h Chen CS, Lai YT, Lai TW, Wu JH, Chen CH, Lee JF, Kao HM. ACS Catal. 2013; 3: 667

24a Cai M, Peng J, Hao W, Ding G. Green Chem. 2011; 13: 190
24b Hao W, Liu H, Yin L, Cai M. J. Org. Chem. 2016; 81: 4244
24c You S, Xiao R, Liu H, Cai M. New J. Chem. 2017; 41: 13862
24d Hao W, Xu Z, Zhou Z, Cai M. J. Org. Chem. 2020; 85: 8522
24e Xu Z, Huang B, Zhou Z, Cai M. Synthesis 2020; 52: 581
24f Zhou Y, Zhou Z, Liu S, Cai M. Mol. Catal. 2022; 526: 112404

25 Lempers HE. B, Sheldon RA. J. Catal. 1998; 175: 62
26 Wang A, Jiang H, Li X. J. Org. Chem. 2011; 76: 6958
27 Schuttler C, Li-Bohmer Z, Harms K, von Zezschwitz P. Org. Lett. 2013; 15: 800
28 Liu Y, Yun X, Zhang-Negrerie D, Huang J, Du Y, Zhang K. Synthesis 2011; 2984
29 Wehrle RJ, Rosen A, Nguyen TV, Koons K, Jump E, Bullard M, Wehrle N, Stockfish A, Hare PM, Atesin A, Atesin TA, Ma L. ACS Omega 2022; 7: 26650
30 Zeng J, Li J, Huang B, Li J, Cai M. J. Organomet. Chem. 2022; 976: 122435

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Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Iso­cyanide as CO Equivalent Leading to 1,2-Diketones

Authors

Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Isocyanide as CO Equivalent Leading to 1,2-Diketones