Nickel-Catalyzed α-1,3-Dienylation of 1,3-Dicarbonyl Compounds with Propargylic Carbonates

Naoki Ishida; Yuka Kamino; Masahiro Murakami

doi:10.1055/a-1282-9731

Synlett, Table of Contents

Synlett 2021; 32(16): 1621-1624
DOI: 10.1055/a-1282-9731

cluster

Modern Nickel-Catalyzed Reactions

Nickel-Catalyzed α-1,3-Dienylation of 1,3-Dicarbonyl Compounds with Propargylic Carbonates

Naoki Ishida ∗

,

Yuka Kamino

,

Masahiro Murakami ∗

Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan Email: naisida@sbchem.kyoto-u.ac.jp Email: murakami@sbchem.kyoto-u.ac.jp

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Abstract

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Abstract

Herein reported is a nickel-catalyzed α-1,3-dienylation reaction of 1,3-dicarbonyl compounds with substituted propargylic (e.g., but-2-ynyl) carbonates. The propargyl unit changes into a 1,3-dienyl unit, which is incorporated at the α-position of the 1,3-dicarbonyl compounds.

Key words

nickel - 1,3-diene - malonate - propargylic carbonate - C–C bond formation

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References

References and Notes

1a The Chemistry of Dienes and Polyenes, Vol. 1. Rappoport Z. Wiley; Chichester: 1997
1b The Chemistry of Dienes and Polyenes, Vol. 2. Rappoport Z. Wiley; Chichester: 2000
1c Corey EJ. Angew. Chem. Int. Ed. 2002; 41: 1650
1d Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668
1e Xiong Y, Sun Y, Zhang G. Tetrahedron Lett. 2018; 59: 347
1f Holmes M, Schwartz LA, Krische MJ. Chem. Rev. 2018; 118: 6026

2 Locascio TM, Tunge JA. Chem. Eur. J. 2016; 22: 18140
3 Ishida N, Hori Y, Okumura S, Murakami M. J. Am. Chem. Soc. 2019; 141: 84
4 O’Broin CQ, Guiry PJ. Org. Lett. 2020; 22: 879

For palladium-catalyzed intramolecular reactions, see:

5a Fournier-Nguefack C, Lhoste P, Sinou D. Synlett 1996; 553
5b Kozawa Y, Mori M. J. Org. Chem. 2003; 68: 8068
5c Ambrogio I, Cacchi S, Fabrizi G, Prastaro A. Tetrahedron 2009; 65: 8916
5d Nemoto T, Zhao Z, Yokosaka T, Suzuki Y, Wu R, Hamada Y. Angew. Chem. Int. Ed. 2013; 52: 2217
5e Daniels DS. B, Jones AS, Thompson AL, Paton R, Anderson A. Angew. Chem. Int. Ed. 2014; 53: 1915
5f Ogiwara Y, Sato K, Sakai N. Org. Lett. 2017; 19: 5296

Reviews on transition-metal-catalyzed reactions of propargylic electrophiles:

6a Tsuji J, Mandai T. Angew. Chem. Int. Ed. 1996; 34: 2589
6b Ma S. Eur. J. Org. Chem. 2004; 1175
6c Guo L.-N, Duan X.-H, Liang Y.-M. Acc. Chem. Res. 2011; 44: 111
6d Yoshida M. Heterocycles 2013; 87: 1835
6e Franckevičius V. Tetrahedron Lett. 2016; 57: 3586
6f Roy R, Saha S. RSC Adv. 2018; 8: 31129
6g O’Broin CQ, Guiry P. J. Org. Chem. 2020; 85: 10321

Selected examples:

7a Behenna DC, Mohr JT, Sherden NH, Marinescu SC, Harned AM, Tani K, Seto M, Ma S, Novák Z, Krout MR, McFadden RM, Roizen JL, Enquist JA, White DE, Levine SR, Petrova KV, Iwashita A, Virgil SC, Stoltz BM. Chem. Eur. J. 2011; 17: 14199
7b Ambrogio I, Cacchi S, Fabrizi G, Goggiamani A, Lazzetti A. Eur. J. Org. Chem. 2015; 3147
7c Oelke AJ, Sun J, Fu GC. J. Am. Chem. Soc. 2012; 134: 2966
7d Watanabe K, Miyazaki Y, Okubo M, Zhou B, Tsuji H, Kawatsura M. Org. Lett. 2018; 20: 5448
7e Tang S, Wei W, Yin D, Poznik M, Chruma JJ. Eur. J. Org. Chem. 2019; 3964
7f O’Broin CQ, Guiry PJ. Org. Lett. 2019; 21: 5402

Selected examples:

8a Jeffery-Luong T, Linstrumelle G. Tetrahedron Lett. 1980; 21: 5019
8b Ruitenberg K, Kleijn H, Elsevier CJ, Meijer J, Vermeer P. Tetrahedron Lett. 1981; 22: 1451
8c Keinan E, Bosch E. J. Org. Chem. 1986; 51: 4006
8d Moriya T, Miyaura N, Suzuki A. Synlett 1994; 149
8e Kimura M, Wakamiya Y, Horino Y, Tamaru Y. Tetrahedron Lett. 1997; 38: 3963
8f Kalek M, Jahansson T, Jezowska M, Stawinski J. Org. Lett. 2010; 12: 4702
8g Molander GA, Sommers EM, Baker SR. J. Org. Chem. 2006; 71: 1563
8h Yoshida M, Ohno S, Namba K. Angew. Chem. Int. Ed. 2013; 52: 13597
8i Smith MK, Tunge JA. Org. Lett. 2017; 19: 5497
8j Wang H, Luo H, Zhang Z, Zheng W.-F, Yin Y, Qian H, Zhang J, Ma S. J. Am. Chem. Soc. 2020; 142: 9763

Selected examples:

9a Tsuji J, Watanabe H, Minami I, Shimizu I. J. Am. Chem. Soc. 1985; 107: 2196
9b Yoshida M, Fujita M, Ishii T, Ihara M. J. Am. Chem. Soc. 2003; 125: 4874
9c Labrosse J.-R, Lhoste P, Delbecq F, Sinou D. Eur. J. Org. Chem. 2003; 2813
9d Ambrogio I, Cacchi S, Fabrizi G. Org. Lett. 2006; 8: 2083
9e Guo L.-N, Duan X.-H, Bi H.-P, Liu X.-Y, Liang Y.-M. J. Org. Chem. 2007; 72: 1538
9f Inuki S, Yoshimitsu Y, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2010; 75: 3831
9g Nishioka N, Koizumi T. J. Polym. Sci., Part A: Polym. Chem. 2011; 49: 642
9h Schröder SP, Taylor NJ, Jackson P, Franckevičius V. Org. Lett. 2013; 15: 3778
9i Nibbs AE, Montgomery TD, Zhu Y, Rawal VH. J. Org. Chem. 2015; 80: 4928
9j Wu T, Chen M, Yang Y. J. Org. Chem. 2017; 82: 11304
9k Kawase A, Omura H, Doi T, Tsukamoto H. Chem. Lett. 2019; 48: 1402
9l Ding L, Gao RD, You S.-L. Chem. Eur. J. 2019; 25: 4330

Selected examples of π-propargyl complexes:

10a Gotzig J, Otto H, Werner H. J. Organomet. Chem. 1985; 287: 247
10b Jia G, Rheingold AL, Meek DW. Organometallics 1989; 8: 1378
10c Wakatsuki Y, Yamazaki H, Maruyama Y, Shimizu I. J. Chem. Soc., Chem. Commun. 1991; 261
10d Krivykh VV, Taits ES, Petrovskii PV, Struchkov YT, Yanovskii AI. Mendeleev Commun. 1991; 1: 103
10e Huang T.-M, Chen J.-T, Lee G.-H, Wang YA. J. Am. Chem. Soc. 1993; 115: 1170
10f Blosser PW, Gallucci JC, Wojcicki A. J. Am. Chem. Soc. 1993; 115: 2994
10g Stang PJ, Crittell CM, Arif AM. Organometallics 1993; 12: 4799
10h Casey CP, Nash JR, Yi CS, Selmeczy AD, Chung S, Powell DR, Hayashi RK. J. Am. Chem. Soc. 1998; 120: 722
10i Cheng Y.-C, Chen Y.-K, Huang T.-M, Yu C.-I, Lee G.-H, Wang Y, Chen J.-T. Organometallics 1998; 17: 2953
10j Norambuena VF. Q, Heeres A, Heeres HJ, Meetsma A, Teuben JH, Hessen B. Organometallics 2008; 27: 5672
10k Nagae H, Kundu A, Tsurugi H, Mashima K. Organometallics 2017; 36: 3061

For the central attack by nucleophile, see:

11a Chen J.-T. Coord. Chem. Rev. 1999; 190-192: 1143
11b Su C.-C, Chen J.-T, Lee G.-H, Wang Y. J. Am. Chem. Soc. 1994; 116: 4999
11c Tsai F.-Y, Hsu R.-H, Huang T.-M, Chen J.-T, Lee G.-H, Wang Y. J. Organomet. Chem. 1996; 520: 85

12 For the formation of π-allylmetals from π-propargylmetals, see ref. 10h,i and 11.
13 For a relevant deprotonation reaction of a π-allylpalladium species, see: Takacs JM, Lawson EC, Clement F. J. Am. Chem. Soc. 1997; 119: 5956
14 α-Dienylation of Malonate 1 with 2: Typical Procedure Ni(cod)₂ (5.5 mg, 0.020 mmol, 5 mol%) and ligand 5 (15.6 mg, 0.030 mmol, 8 mol%) were placed in a vial. Acetonitrile (2 mL) was added, and the mixture was stirred at room temperature for 5 min. Then, malonate 1 (69.7 mg, 0.40 mmol) and propargyl carbonate 2 (88.5 mg, 0.52 mmol, 1.3 equiv) were added to the mixture, which was stirred at 80 °C for 24 h. After cooled to room temperature, the reaction mixture was passed through a pad of silica gel, which was eluted with ethyl acetate. The filtrate was evaporated to dryness under reduced pressure. The residue was purified by preparative thin-layer chromatography (PTLC; eluent: hexane/ethyl acetate = 10:1) to give a colorless oil (80.4 mg), which was estimated by ¹H NMR spectroscopy to contain 3 (0.33 mmol, 81%) and 4 (0.029 mmol, 7%). ¹H NMR (400 MHz, CDCl₃): δ = 1.26 (t, J = 7.0 Hz, 6 H), 1.63 (s, 3 H), 4.22 (q, J = 7.2 Hz, 4 H), 5.02 (s, 1 H), 5.09 (d, J = 10.8 Hz, 1 H), 5.38 (d, J = 17.2 Hz, 1 H), 5.42 (s, 1 H), 6.31 (dd, J = 17.2, 11.2 Hz, 1 H). ¹³C NMR (101 MHz, CDCl₃): δ = 14.1, 21.2, 58.9, 61.7, 114.1, 115.8, 136.2, 145.2, 171.1. HRMS (APCI⁺): m/z calcd for C₁₂H₁₉O₄ [M + H]⁺: 227.1283; found: 227.1279. IR (ATR): 2983, 1728, 1248, 1219, 1101, 1018 cm^–1.

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