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Synthesis 2022; 54(16): 3631-3641
DOI: 10.1055/a-1801-3656
DOI: 10.1055/a-1801-3656
paper
Palladium-Catalyzed Three-Component 1,4-Carboarylation of 1,3-Enynes with Malonic Esters and Aryl Iodides
This work was supported by the National Natural Science Foundation of China (NSFC) (22001251, 21871258, 21922112), the National Key Research and Development Program of China (2017YFA0700103), and the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20000000).
Abstract
Ionic 1,4-difunctionalization of 1,3-enynes has often been conducted with strong nucleophiles or 1,3-enynes that are activated by an electron-withdrawing group. In this work, a palladium-catalyzed three-component ionic 1,4-carboarylation of 1,3-enynes is reported with arylated 1,3-enynes as the substrates. This method can afford various tetrasubstituted allenes with different functionalities. The palladium salt might play a key dual role in the reaction: as the catalyst to catalyze the cross-coupling reaction and as a Lewis acid to facilitate the nucleophilic attack. The synthetic value of this method is demonstrated by the further cyclization, decoration, and hydrolysis of the allene products.
Key words
1,3-enynes - tetrasubstituted allenes - 1,4-difunctionalization - ionic reaction - palladiumSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1801-3656.
- Supporting Information
Publication History
Received: 09 February 2022
Accepted after revision: 17 March 2022
Accepted Manuscript online:
17 March 2022
Article published online:
12 May 2022
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References
- 1a Aubert C, Fensterbank L, Garcia P, Malacria M, Simonneau A. Chem. Rev. 2011; 111: 1954
- 1b Hoffmann-Röder A, Krause N. Angew. Chem. Int. Ed. 2004; 43: 1196
- 1c Ma S. Chem. Rev. 2005; 105: 2829
- 1d Ma S. Acc. Chem. Res. 2009; 42: 1679
- 1e Ye J, Ma S. Org. Chem. Front. 2014; 1: 1210
- 1f Yu S, Ma S. Angew. Chem. Int. Ed. 2012; 51: 3074
- 1g Modern Allene Chemistry, Vols. 1 and 2. Krause N, Hashimi AS. K. Wiley-VCH; Weinheim: 2004
- 1h Yu S, Ma S. Chem. Commun. 2011; 47: 5384
- 1i Sakaguchi K, Nishioka Y, Kinashi N, Yukihira N, Shinada T, Nishimura T, Hashimoto H, Katsumura S. Synthesis 2020; 52: 3007
- 1j Moberg C. Synthesis 2020; 52: 3129
- 2a Ishikawa T, Manabe S, Aikawa T, Kudo T, Saito S. Org. Lett. 2004; 6: 2361
- 2b Ito H, Sasaki Y, Sawamura M. J. Am. Chem. Soc. 2008; 130: 15774
- 2c Kessler SN, Backvall JE. Angew. Chem. Int. Ed. 2016; 55: 3734
- 2d Qian D, Wu L, Lin Z, Sun J. Nat. Commun. 2017; 8: 567
- 2e Xu B, Hammond GB. Angew. Chem. Int. Ed. 2008; 47: 689
- 2f Yang Z, Hao WJ, Wang SL, Zhang JP, Jiang B, Li G, Tu SJ. J. Org. Chem. 2015; 80: 9224
- 2g Zhao J, Szabo KJ. Angew. Chem. Int. Ed. 2016; 55: 1502
- 3a Doye S, Hotopp T, Wartchow R, Winterfeldt E. Chem. Eur. J. 1998; 4: 1480
- 3b Li Z, Boyarskikh V, Hansen JH, Autschbach J, Musaev DG, Davies HM. J. Am. Chem. Soc. 2012; 134: 15497
- 3c Liu H, Leow D, Huang KW, Tan CH. J. Am. Chem. Soc. 2009; 131: 7212
- 3d Marshall JA, Wang XJ. J. Org. Chem. 1991; 56: 6264
- 3e Mundal DA, Lutz KE, Thomson RJ. J. Am. Chem. Soc. 2012; 134: 5782
- 3f Sherry BD, Toste FD. J. Am. Chem. Soc. 2004; 126: 15978
- 4a Kimura M, Mori Y, Kawabata T, Onodera G. Synthesis 2016; 48: 2385
- 4b Ma S, Zhang J, Lu L. Chem. Eur. J. 2003; 9: 2447
- 4c Nishimura A, Tamai E, Ohashi M, Ogoshi S. Chem. Eur. J. 2014; 20: 1
- 4d Todo H, Terao J, Watanabe H, Kuniyasu H, Kambe N. Chem. Commun. 2008; 1332
- 4e Wang H.-Y, Zhang W, Schienebeck CM, Bennett SR, Tang W. Org. Chem. Front. 2014; 1: 386
- 4f Whitehead DC, Yousefi R, Jaganathan A, Borhan B. J. Am. Chem. Soc. 2010; 132: 3298
- 4g Zhang W, Xu H, Xu H, Tang W. J. Am. Chem. Soc. 2009; 131: 3832
- 5a Chu WD, Zhang L, Zhang Z, Zhou Q, Mo F, Zhang Y, Wang J. J. Am. Chem. Soc. 2016; 138: 14558
- 5b Huang Y, Del Pozo J, Torker S, Hoveyda AH. J. Am. Chem. Soc. 2018; 140: 2643
- 5c Mainetti E, Fensterbank L, Malacria M. Synlett 2002; 923
- 5d Qian H, Yu X, Zhang J, Sun J. J. Am. Chem. Soc. 2013; 135: 18020
- 5e Sang HL, Yu S, Ge S. Org. Chem. Front. 2018; 5: 1284
- 5f Wang Z, Li X, Huang Y. Angew. Chem. Int. Ed. 2013; 52: 14219
- 6a Cai Y, Chen J, Huang Y. Org. Lett. 2021; 23: 9251
- 6b Chen Y, Wang J, Lu Y. Chem. Sci. 2021; 12: 11316
- 6c Chen Y, Zhu K, Huang Q, Lu Y. Chem. Sci. 2021; 12: 13564
- 6d Dong XY, Zhan TY, Jiang SP, Liu XD, Ye L, Li ZL, Gu QS, Liu XY. Angew. Chem. Int. Ed. 2021; 60: 2160
- 6e He FS, Bao P, Yu F, Zeng LH, Deng WP, Wu J. Org. Lett. 2021; 23: 7472
- 6f Huang J, Jia Y, Li X, Duan J, Jiang ZX, Yang Z. Org. Lett. 2021; 23: 2314
- 6g Shen H, Xiao H, Zhu L, Li C. Synlett 2020; 31: 41
- 6h Song Y, Fu C, Ma S. ACS Catal. 2021; 11: 10007
- 6i Song Y, Song S, Duan X, Wu X, Jiang F, Zhang Y, Fan J, Huang X, Fu C, Ma S. Chem. Commun. 2019; 55: 11774
- 6j Wang F, Wang D, Zhou Y, Liang L, Lu R, Chen P, Lin Z, Liu G. Angew. Chem. Int. Ed. 2018; 57: 7140
- 6k Xu T, Wu S, Zhang QN, Wu Y, Hu M, Li JH. Org. Lett. 2021; 23: 8455
- 6l Ye C, Li Y, Zhu X, Hu S, Yuan D, Bao H. Chem. Sci. 2019; 10: 3632
- 6m Zeng Y, Chiou MF, Zhu X, Cao J, Lv D, Jian W, Li Y, Zhang X, Bao H. J. Am. Chem. Soc. 2020; 142: 18014
- 6n Zhang K.-F, Bian K.-J, Li C, Sheng J, Li Y, Wang X.-S. Angew. Chem. Int. Ed. 2019; 58: 5069
- 6o Zhao Y, Wang JL, Zhang Z, Li XS, Niu ZJ, Liu XY. J. Org. Chem. 2021; 86: 18056
- 6p Zhu X, Deng W, Chiou M.-F, Ye C, Jian W, Zeng Y, Jiao Y, Ge L, Li Y, Zhang X, Bao H. J. Am. Chem. Soc. 2019; 141: 548
- 7a Bao X, Ren J, Yang Y, Ye X, Wang B, Wang H. Org. Biomol. Chem. 2020; 18: 7977
- 7b Liao Y, Yin X, Wang X, Yu W, Fang D, Hu L, Wang M, Liao J. Angew. Chem. Int. Ed. 2020; 59: 1176
- 7c Mori Y, Onodera G, Kimura M. Chem. Lett. 2014; 43: 97
- 7d Qian D, Zhang J. Acc. Chem. Res. 2020; 53: 2358
- 7e Taj Muhammad M, Jiao Y, Ye C, Chiou MF, Israr M, Zhu X, Li Y, Wen Z, Studer A, Bao H. Nat. Commun. 2020; 11: 416
- 7f Terao J, Bando F, Kambe N. Chem. Commun. 2009; 7336
- 7g Tomida Y, Nagaki A, Yoshida J. J. Am. Chem. Soc. 2011; 133: 3744
- 7h Wang M, Liu ZL, Zhang X, Tian PP, Xu YH, Loh TP. J. Am. Chem. Soc. 2015; 137: 14830
- 7i Xiao Y, Zhang J. Chem. Commun. 2010; 46: 752
- 7j Yao Q, Liao Y, Lin L, Lin X, Ji J, Liu X, Feng X. Angew. Chem. Int. Ed. 2016; 55: 1859
- 7k Ye J, Liao Y, Huang H, Liu Y, Fang D, Wang M, Hu L, Liao J. Chem. Sci. 2021; 12: 3032
- 7l Yu SJ, Sang HL, Zhang SQ, Hong X, Ge SZ. Commun. Chem. 2018; 1: 64
- 8 Ma S, He Q, Jin X. Synlett 2005; 514
- 9 Yu X, Ren H, Xiao Y, Zhang J. Chem. Eur. J. 2008; 14: 8481
- 10a Poulsen PH, Li Y, Lauridsen VH, Jørgensen DK. B, Palazzo TA, Meazza M, Jørgensen KA. Angew. Chem. Int. Ed. 2018; 57: 10661
- 10b Ma Z.-G, Wei J.-L, Lin J.-B, Wang G.-J, Zhou J, Chen K, Fan C.-A, Zhang S.-Y. Org. Lett. 2019; 21: 2468
- 11 Okrasa K, Levy C, Wilding M, Goodall M, Baudendistel N, Hauer B, Leys D, Micklefield J. Angew. Chem. Int. Ed. 2009; 48: 7691
- 12 Li Z, Wang M, Shi Z. Angew. Chem. Int. Ed. 2021; 60: 186
- 13 Xiao Y, Zhang J. Chem. Commun. 2009; 3594
- 14 The 1,3-enynes were synthesized according to our previous work.6l,p