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Synthesis 2022; 54(12): 2787-2798
DOI: 10.1055/a-1750-3080
DOI: 10.1055/a-1750-3080
feature
Dehydrative and Decarboxylative Coupling of Alkynoic Acids with Allylic Alcohols
We gratefully acknowledge financial support from the National Natural Science Foundation of China (21702108), the Natural Science Foundation of Jiangsu Province, China (BK20211257, BK20160977), and the Six Talent Peaks Project in Jiangsu Province (YY-033).
Dedicated to Prof. You Huang on the occasion of his 60th birthday
Abstract
A direct dehydroxylative and decarboxylative coupling between a large number of allylic alcohols and alkynoic acids was realized affording 1,4-enyne motifs in high efficiency. In this reaction, calcium-promoted C–OH bond cleavage was crucial, which facilitated the sequential decarboxylation, and thus enabled the palladium-catalyzed allyl–alkynyl coupling, which occurred in an environmentally benign manner tolerating a wide variety of functional groups. This protocol has been successfully used in preparing anticancer active rooperol derivatives in gram scale.
Key words
dehydrative cross-coupling - C–OH bond cleavage - decarboxylation - 1,4-enynes - green chemistry - cooperative catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1750-3080.
- Supporting Information
Publication History
Received: 11 November 2021
Accepted after revision: 25 January 2022
Accepted Manuscript online:
25 January 2022
Article published online:
08 March 2022
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References
- 1a Perry IB, Brewer TF, Sarver PJ, Schultz DM, DiRocco DA, MacMillan DW. C. Nature 2018; 560: 70
- 1b Xuan J, Zhang Z.-G, Xiao W.-J. Angew. Chem. Int. Ed. 2015; 54: 15632
- 1c Hu RM, Han DY, Li N, Huang J, Feng Y, Xu DZ. Angew. Chem. Int. Ed. 2020; 59: 3876
- 1d Jiang J, Xiao F, He W.-M, Wang L. Chin. Chem. Lett. 2021; 32: 1637
- 1e Chen X, Xiao F, He W. Org. Chem. Front. 2021; 8: 5206
- 2a Idris MA, Lee S. Synthesis 2020; 52: 2277
- 2b Patra T, Maiti D. Chem. Eur. J. 2017; 23: 7382
- 2c Park K, Lee S. RSC Adv. 2013; 3: 14165
- 2d Dzik WI, Lange PP, Gooßen LJ. Chem. Sci. 2012; 3: 2671
- 3a Zhang W.-W, Zhang X.-G, Li J.-H. J. Org. Chem. 2010; 75: 5259
- 3b Yang Y, Lim YH, Robins EG, Johannes CW. RSC Adv. 2016; 6: 72810
- 4 Chang S, Liu Y, Yin SZ, Dong LL, Wang JF. New J. Chem. 2019; 43: 5357
- 5 Moon J, Jeong M, Nam H, Ju J, Moon JH, Jung HM, Lee S. Org. Lett. 2008; 10: 945
- 6a Mousa AH, Fleckhaus A, Kondrashov M, Wendt OF. J. Organomet. Chem. 2017; 845: 157
- 6b Reddy PV, Srinivas P, Annapurna M, Bhargava S, Wagler J, Mirzadeh N, Kantam ML. Adv. Synth. Catal. 2013; 355: 705
- 6c Li X, Yang F, Wu Y. J. Org. Chem. 2013; 78: 4543
- 6d Li X, Yang F, Wu Y. RSC Adv. 2014; 4: 13738
- 6e Yang Y, Lim YH, Robins EG, Johannes CW. RSC Adv. 2016; 6: 72810
- 6f Moon J, Jang M, Lee S. J. Org. Chem. 2009; 74: 1403
- 6g Kim H, Lee PH. Adv. Synth. Catal. 2009; 351: 2827
- 6h Tartaggia S, Lucchi OD, Gooßen LJ. Eur. J. Org. Chem. 2012; 1431
- 7 For a recent example concerning nickel-catalyzed version, see: Son Y, Kim H.-S, Lee J.-H, Jang J, Lee C.-F, Lee S. Tetrahedron Lett. 2017; 58: 1413
- 8a Pan D.-L, Zhang C, Ding S.-T, Jiao N. Eur. J. Org. Chem. 2011; 4751
- 8b Park J, Jung D, Kim H.-S, Na K, Lee S. Catal. Commun. 2017; 99: 83
- 8c Zhao D.-B, Gao C, Su X.-Y, He Y.-Q, You J.-S, Xue Y. Chem. Commun. 2010; 46: 9049
- 8d Wang X, Wang Z, Xie Z, Zhang G, Zhang W, Gao Z. RSC Adv. 2016; 6: 109296
- 8e Kumar MR, Irudayanathan FM, Moon JH, Lee S. Adv. Synth. Catal. 2013; 355: 3221
- 8f Li TY, Qu X.-M, Zhu Y, Sun P, Yang H.-L, Shan Y.-Q, Zhang H.-X, Liu DF, Zhang X, Mao J.-C. Adv. Synth. Catal. 2011; 353: 2731
- 9a Yu S, Cho E, Kim J, Lee S. J. Org. Chem. 2017; 82: 11150
- 9b Bhojane JM, Jadhav VG, Nagarkar JM. New J. Chem. 2017; 41: 6775
- 9c Balsane KE, Gund SH, Nagarkar JM. Catal. Commun. 2018; 104: 78
- 9d Howard A, Klemann S, Kolling S, Little K, Plasek E, Kalyani D. Synthesis 2019; 51: 1603
- 10a Hwang J, Park K, Choe J, Min H, Song KH, Lee S. J. Org. Chem. 2014; 79: 3267
- 10b Tummanapalli S, Muthuraman P, Vangapandu DN, Shanmugavel G, Kambampati S, Lee KW. RSC Adv. 2015; 5: 49392
- 11a Chen Z.-M, Nervig CS, Deluca RJ, Sigman MS. Angew. Chem. Int. Ed. 2017; 56: 6651
- 11b Bernhard Y, Thomson B, Ferey V, Sauthier M. Angew. Chem. Int. Ed. 2017; 56: 7460
- 11c Schlepphorst C, Maji B, Glorius F. ACS Catal. 2016; 6: 4184
- 11d Kita Y, Kavthe RD, Oda H, Mashima K. Angew. Chem. Int. Ed. 2016; 55: 1098
- 11e Suzuki Y, Sun B, Sakata K, Yoshino T, Matsunaga S, Kanai M. Angew. Chem. Int. Ed. 2015; 54: 9944
- 11f Xu Q, Chen J, Tian H, Yuan X, Li S, Zhou C, Liu J. Angew. Chem. Int. Ed. 2014; 53: 225
- 11g Walton JW, Williams JM. J. Angew. Chem. Int. Ed. 2012; 51: 12166
- 11h Jin J, MacMillan DW. C. Nature 2015; 525: 87
- 11i Terrett JA, Cuthbertson JD, Shurtleff VW, MacMillan DW. C. Nature 2015; 524: 330
- 12 Masuda Y, Ito M, Murakami M. Chem. Lett. 2021; 50: 1030
- 13a Wu L.-J, Song R.-J, Luo S, Li J.-H. Angew. Chem. Int. Ed. 2018; 57: 13308
- 13b Pradhan TR, Kim HW, Park JK. Angew. Chem. Int. Ed. 2018; 57: 9930
- 13c Almasalma AA, Mejia E. Chem. Eur. J. 2018; 24: 12269
- 13d Cui X.-Y, Ge Y.-C, Tan SM, Jiang H, Tan D, Lu Y, Lee R, Tan C.-H. J. Am. Chem. Soc. 2018; 140: 8448
- 13e Yang S, Rui K.-H, Tang X.-Y, Xu Q, Shi M. J. Am. Chem. Soc. 2017; 139: 5957
- 14a Drewes S, Liebenberg RW. U. S. Patent 4652636, 1987
- 14b Liebenberg RW, Bouic PB, Kruger PJ. D, de Vos Albrecht CF. U. S. Patent 5609874, 1997
- 14c Daniewski WM, Danikiewicz W, Gołębiewski WM, Gucma M, Łysik A, Grodner J, Przybysz E. Nat. Prod. Commun. 2012; 7: 917
- 15a Rayabarapu DK, Tunge JA. J. Am. Chem. Soc. 2005; 127: 13510
- 15b Choe J, Yang J, Park K, Palani T, Lee S. Tetrahedron Lett. 2012; 53: 6908
- 15c Chen H, Deng M.-Z. J. Organomet. Chem. 2000; 603: 189
- 15d Leadbeater NE. J. Org. Chem. 2001; 66: 7539
- 15e Bieber LW, da Silva MF. Tetrahedron Lett. 2007; 48: 7088
- 15f Kumar GG. K. S. N, Laali KK. Org. Biomol. Chem. 2012; 10: 7347
- 15g Ma S, Zhang A. J. Org. Chem. 2002; 67: 2287
- 15h Nishikawa T, Isobe M. Biosci. Biotechnol. Biochem. 1999; 63: 238
- 15i Kiyotsuka Y, Kobayashi Y. J. Org. Chem. 2009; 74: 7489
- 16a Mao J, Zhang J, Jiang H, Bellomo A, Zhang M, Gao Z, Dreher SD, Walsh PJ. Angew. Chem. Int. Ed. 2016; 55: 2526
- 16b Meng J, Fan L.-F, Han Z.-Y, Gong L.-Z. Chem 2018; 4: 1047
- 17a Xie P, Li S, Liu Y, Cai X, Wang J, Yang X, Loh T.-P. Org. Lett. 2020; 22: 31
- 17b Xie P, Sun Z, Li S, Zhang L, Cai X, Fu W, Yang X, Liu Y, Wo X, Loh T.-P. Org. Lett. 2020; 22: 1599
- 17c Xie P, Sun Z, Li S, Cai X, Qiu J, Fu W, Gao C, Wu S, Yang X, Loh T.-P. Org. Lett. 2020; 22: 4893
- 17d Xie P, Wang J, Liu Y, Fan J, Wo X, Fu W, Sun Z, Loh T.-P. Nat. Commun. 2018; 9: 1321
- 18 Pitzer L, Schäfers F, Glorius F. Angew. Chem. Int. Ed. 2019; 58: 8572
For selected recent reviews, see:
For selected recent examples concerning palladium-catalyzed versions, see:
For selected recent examples concerning copper-catalyzed versions, see:
For selected examples, see;
For some selected recent literature, see:
1,4-Enynes served as building block in organic synthesis, see:
For selected examples of biologically and pharmaceutically active molecules involving 1,4-enynes, see:
For selected examples for preparing 1,4-enynes, see:
For some selected examples, see: