Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst

Keiichiro Iizumi; Miki B. Kurosawa; Ryota Isshiki; Kei Muto; Junichiro Yamaguchi

doi:10.1055/s-0040-1705943

Synlett, Table of Contents

Synlett 2021; 32(15): 1555-1559
DOI: 10.1055/s-0040-1705943

cluster

Modern Nickel-Catalyzed Reactions

Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst

Keiichiro Iizumi

^aDepartment of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan Email: junyamaguchi@waseda.jp

,

Miki B. Kurosawa

^aDepartment of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan Email: junyamaguchi@waseda.jp

,

Ryota Isshiki

^aDepartment of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan Email: junyamaguchi@waseda.jp

,

Kei Muto

^bInstitute for Advanced Study, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan

,

Junichiro Yamaguchi ∗

^aDepartment of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan Email: junyamaguchi@waseda.jp

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Abstract

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Abstract

A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.

Key words

nickel catalysis - cyanation - aromatic esters - aminoacetonitriles - coupling reaction

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References

References and Notes

1a Fleming FF, Wang Q. Chem. Rev. 2003; 103: 2035
1b Fleming FF, Yao L, Ravikumar PC, Funk L, Shook BC. J. Med. Chem. 2010; 53: 7902

2a Ellis GP, Romney-Alexander TM. Chem. Rev. 1987; 87: 779
2b Anbarasan P, Schareina T, Beller M. Chem. Soc. Rev. 2011; 40: 5049
2c Wen Q, Jin J, Zhang L, Luo Y, Lu P, Wang Y. Tetrahedron Lett. 2014; 55: 1271
2d Yan G, Zhang Y, Wang J. Adv. Synth. Catal. 2017; 359: 4068

3a Sakamoto T, Ohsawa K. J. Chem. Soc., Perkin Trans. 1 1999; 2323
3b Jia X, Yang D, Zhang S, Cheng J. Org. Lett. 2009; 11: 4716

4a Maligres PE, Waters MS, Fleitz F, Askin D. Tetrahedron Lett. 1999; 40: 8193
4b Chidambaram R. Tetrahedron Lett. 2004; 45: 1441
4c Jensen RS, Gajare AS, Toyota K, Yoshifuji M, Ozawa F. Tetrahedron Lett. 2005; 46: 8645
4d Littke A, Soumeillant M, Kaltenbach RF, Cherney RJ, Tarby CM, Kiau S. Org. Lett. 2007; 9: 1711
4e Martin MT, Liu B, Cooley BE. Jr, Eaddy JF. Tetrahedron Lett. 2007; 48: 2555
4f Buono FG, Chidambaram R, Mueller RH, Waltermire RE. Org. Lett. 2008; 10: 5325

5a Takagi K, Okamoto T, Sakakibara Y, Oka A. Chem. Lett. 1973; 471
5b Sakakibara Y, Okuda F, Shimobayashi A, Kirino K, Sakai M, Uchino N, Takagi K. Bull. Chem. Soc. Jpn. 1988; 61: 1985
5c Percec V, Bae J.-Y, Hill DH. J. Org. Chem. 1995; 60: 6895
5d Anderson BA, Bell EC, Ginah FO, Harn NK, Pagh LM, Wepsiec JP. J. Org. Chem. 1998; 63: 8224
5e Yang C, Williams JM. Org. Lett. 2004; 6: 2837
5f Cristau H.-J, Ouali A, Spindler J.-F, Taillefer M. Chem. Eur. J. 2005; 11: 2483

6a Chatani N, Hanafusa T. J. Org. Chem. 1986; 51: 4714
6b Sundermeier M, Mutyala S, Zapf A, Spannenberg A, Beller M. J. Organomet. Chem. 2003; 684: 50

For methods using K₄Fe(CN)₆, see:

7a Schareina T, Zapf A, Beller M. Chem. Commun. 2004; 1388
7b Mariampillai B, Alliot J, Li M, Lautens M. J. Am. Chem. Soc. 2007; 129: 15372
7c Yeung PY, So CM, Lau CP, Kwong FY. Angew. Chem. Int. Ed. 2010; 49: 8918
7d Senecal TD, Shu W, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 10035

For reviews on organic cyanating reagents, see:

8a Kim J, Kim HJ, Chang S. Angew. Chem. Int. Ed. 2012; 51: 11948
8b Nauth AM, Opatz T. Org. Biomol. Chem. 2019; 17: 11

For methods using alkyl nitriles, see:

8c Luo F.-H, Chu C.-I, Cheng C.-H. Organometallics 1998; 17: 1025
8d Wen Q, Jin J, Hu B, Lu P, Wang Y. RSC Adv. 2012; 2: 6167
8e Yu P, Morandi M. Angew. Chem. Int. Ed. 2017; 56: 15693
8f Ueda Y, Tsujimoto N, Yurino T, Tsurugi H, Mashima K. Chem. Sci. 2019; 10: 994

For methods using other organic cyanating reagents, see:

8g Jiang Z, Huang Q, Chen S, Long L, Zhou X. Adv. Synth. Catal. 2012; 354: 589
8h Zheng S, Yu C, Shen Z. Org. Lett. 2012; 14: 3644
8i Jiang X, Wang J.-M, Zhang Y, Chen Z, Zhu Y.-M, Ji S.-J. Tetrahedron 2015; 71: 4883
8j Chen H, Sun S, Liu YA, Liao X. ACS Catal. 2020; 10: 1397

9a Gan Y, Wang G, Xie X, Liu Y. J. Org. Chem. 2018; 83: 14036
9b Xu W, Xu Q, Li J. Org. Chem. Front. 2015; 2: 231

10 Kotani S, Sakamoto M, Osakama K, Nakajima M. Eur. J. Org. Chem. 2015; 6606
11 Takise R, Itami K, Yamaguchi J. Org. Lett. 2016; 18: 4428
12 Wang L, Wang Y, Shen J, Chen Q, He M.-Y. Org. Biomol. Chem. 2018; 16: 4816

13a Takise R, Muto K, Yamaguchi J. Chem. Soc. Rev. 2017; 46: 5864
13b Shi S, Nolan SP, Szostak M. Acc. Chem. Res. 2018; 51: 2589
13c Guo L, Rueping M. Chem. Eur. J. 2018; 24: 7794
13d Lu H., Yu T.-Y., Xu P.-F., Wei H.; Chem. Rev.; 2020, in press; DOI: 10.1021/acs.chemrev.0c00153

For selected examples of decarbonylative C–C bond formations, see:

14a Chatani N, Tatamidani H, Ie Y, Kakiuchi F, Murai S. J. Am. Chem. Soc. 2001; 123: 4849
14b Gooßen LJ, Paetzold J. Angew. Chem, Int. Ed. 2002; 41: 1237
14c Gooßen LJ, Paetzold J. Angew. Chem. Int. Ed. 2004; 43: 1095
14d Amaike K, Muto K, Yamaguchi J, Itami K. J. Am. Chem. Soc. 2012; 134: 13573
14e Meng L, Kamada Y, Muto K, Yamaguchi J, Itami K. Angew. Chem. Int. Ed. 2013; 52: 10048
14f Muto K, Yamaguchi J, Musaev DG, Itami K. Nat. Commun. 2015; 6: 7508
14g Okita T, Kumazawa K, Takise R, Muto K, Itami K, Yamaguchi J. Chem. Lett. 2017; 46: 218
14h Isshiki R, Takise R, Itami K, Muto K, Yamaguchi J. Synlett 2017; 28: 2599
14i Liu X, Jia J, Rueping M. ACS Catal. 2017; 7: 4491
14j Okita T, Muto K, Yamaguchi J. Org. Lett. 2018; 20: 3132
14k Chatupheeraphat A, Liao H.-H, Srimontree W, Guo L, Minenkov Y, Poater A, Caballo L, Rueping M. J. Am. Chem. Soc. 2018; 140: 3724
14l Masson-Makdissi J, Vandavasi JK, Newman SG. Org. Lett. 2018; 20: 4094
14m Matsushita K, Takise R, Muto K, Yamaguchi J. Sci. Adv. 2020; 6: eaba7614

For selected examples of decarbonylative carbon–heteroatom bond formations, see:

15a Pu X, Hu J, Zhao Y, Shi Z. ACS Catal. 2016; 6: 6692
15b Guo L, Chatupheeraphat A, Rueping M. Angew. Chem. Int. Ed. 2016; 55: 11810
15c Takise R, Isshiki R, Muto K, Itami K, Yamaguchi J. J. Am. Chem. Soc. 2017; 139: 3340
15d Yue H, Guo L, Liao H.-H, Cai Y, Zhu C, Rueping M. Angew. Chem. Int. Ed. 2017; 56: 4284
15e Isshiki R, Muto K, Yamaguchi J. Org. Lett. 2018; 20: 1150
15f Malapit CA, Borrell M, Milbauer MW, Brigham CE, Sanford MS. J. Am. Chem. Soc. 2020; 142: 5918

16a Takise R, Muto K, Yamaguchi J, Itami K. Angew. Chem. Int. Ed. 2014; 53: 6791
16b Koch E, Takise R, Studer A, Yamaguchi J, Itami K. Chem. Commun. 2015; 51: 855

17a Chatupheeraphat A, Liao H.-H, Lee S.-C, Rueping M. Org. Lett. 2017; 19: 4255

For a related reaction using aroyl chlorides, see:

17b Wang Z, Wang X, Ura Y, Nishihara Y. Org. Lett. 2019; 21: 6779

18 A main reason for the modest yield of some products was the decomposition of the phenyl esters to the corresponding carboxylic acids.
19 2-Naphthonitrile (3A); Typical Procedure A 20-mL glass vessel, equipped with a J. Young O-ring tap and a magnetic stirring bar, was charged with Ni(OAc)₂·4 H₂O (10.0 mg, 0.040 mmol, 10 mol%) and Na₂CO₃ (63.6 mg, 0.60 mmol, 1.5 equiv). The vessel was evacuated and its contents were dried with a heat gun. The vessel was then cooled to r.t., and filled with N₂ gas. Phenyl 2-naphthoate (1A; 99.3 mg, 0.40 mmol, 1.0 equiv), 2-morpholinoacetonitrile (2a: 100.9 mg, 0.80 mmol, 2.0 equiv), and dcypt (38.1 mg, 0.080 mmol, 20 mol%) were added, and the vessel was evacuated and refilled with N₂ gas three times. Toluene (1.6 mL) was added, and the vessel was sealed with the O-ring tap and heated at 160 °C in a nine-well reaction block for 24 h with stirring. The mixture was then cooled to r.t. and passed through a short silica-gel pad with EtOAc as an eluent. The filtrate was concentrated in vacuo, and the residue was purified by preparative TLC (hexane–EtOAc, 4:1) to give a white solid; yield: 46.3 mg (76%) (caution! The reaction should be conducted in a well-functioning fume hood to avoid exposure to the CO gas generated by the reaction. After the reaction, the vessel should be opened in the fume hood for the same reason.) ¹H NMR (400 MHz, CDCl₃): δ = 8.23 (s, 1 H), 7.93–7.87 (m, 3 H), 7.67–7.58 (m, 3 H). ¹³C NMR (101 MHz, CDCl₃): δ = 134.6, 134.1, 132.2, 129.1, 129.0, 128.4, 128.0, 127.6, 126.3, 119.2, 109.3. HRMS (DART): m/z [M + NH₄]⁺ calcd for C₁₁H₁₁N₂: 171.0917; found: 171.0915.

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