Ni^IICl(1-Naphthyl)(PCy₃)₂, An Air-Stable σ-Ni^II Precatalyst for Quantitative Cross-Coupling of Aryl C–O Electrophiles with Aryl Neopentylglycolboronates

Abstract

Advances in nickel catalysis have enabled the employment of the widely available and environmentally benign phenol derivatives as aryl electrophiles in Suzuki–Miyaura cross-coupling reactions. Ni^II-phosphine complexes such as Ni^IICl₂(PPh₃)₂, Ni^IICl₂(dppf), Ni^IICl₂(dppe), Ni^IICl₂(dppp), Ni^IICl₂(PCy₃)₂ and π-Ni⁰ complexes, the classic being Ni(COD)₂/PCy₃, both classes mostly in the presence of a mixed ligand, are some of the most successful precatalysts employed in the cross-coupling of aryl mesylates, sulfamates, carboxylic esters, carbonates, carbamates and methyl ethers with aryl boronic acids, boroxines and neopentylglycolboronates. Here we report that the highly reactive but bench-stable σ-Ni^II complex, Ni^IICl(1-naphthyl)(PCy₃)₂ (where σ refers to the Ni–C bond), exhibits higher efficiency than all previously reported precatalysts and facilitates the quantitative cross-coupling of all six C–O electrophiles mentioned above in reaction times of 0.5 to 24 hours.

Key words

nickel - C–O electrophiles - precatalysts - cross-coupling - quantitative

• References

• 1a Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A.-M, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346
• 1b Han F.-S. Chem. Soc. Rev. 2013; 42: 5270
• 1c Mesganaw T, Garg NK. Org. Process Res. Dev. 2013; 17: 29
• 1d Yamaguchi J, Muto K, Itami K. Eur. J. Org. Chem. 2013; 19
• 1e Cornella J, Zarate C, Martin R. Chem. Soc. Rev. 2014; 43: 8081
• 1f Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
• 1g Su B, Cao Z.-C, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
• 1h Standley EA, Tasker SZ, Jensen KL, Jamison TF. Acc. Chem. Res. 2015; 48: 1503
• 1i Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
• 2 Quasdorf KW, Riener M, Petrova KV, Garg NK. J. Am. Chem. Soc. 2009; 131: 17748
• 3 Antoft-Finch A, Blackburn T, Snieckus V. J. Am. Chem. Soc. 2009; 131: 17750
• 4a Percec V, Bae JY, Hill DH. J. Org. Chem. 1995; 60: 1060
• 4b Percec V, Bae JY, Zhao MY, Hill DH. J. Org. Chem. 1995; 60: 1066
• 4c Percec V, Golding GM, Smidrkal J, Weichold O. J. Org. Chem. 2004; 69: 3447
• 4d Zim D, Lando VR, Dupont J, Monteiro AL. Org. Lett. 2001; 3: 3049
• 4e Gao H, Li Y, Zhou YG, Han FS, Lin YJ. Adv. Synth. Catal. 2011; 353: 309
• 4f Kobayashi Y, Mizojiri R. Tetrahedron Lett. 1996; 37: 8531
• 5a Baghbanzadeh M, Pilger C, Kappe CO. J. Org. Chem. 2011; 76: 1507
• 5b Quasdorf KW, Antoft-Finch A, Liu P, Silberstein AL, Komaromi A, Blackburn T, Ramgren SD, Houk KN, Snieckus V, Garg NK. J. Am. Chem. Soc. 2011; 133: 6352
• 5c Chen G.-J, Han F.-S. Eur. J. Org. Chem. 2012; 3575
• 5d Ke H, Chen X, Zou G. J. Org. Chem. 2014; 79: 7132
• 6a Quasdorf KW, Tian X, Garg NK. J. Am. Chem. Soc. 2008; 130: 14422
• 6b Guan B.-T, Wang Y, Li B.-J, Yu D.-G, Shi Z.-J. J. Am. Chem. Soc. 2008; 130: 14468
• 7 Kuwano R, Shimizu R. Chem. Lett. 2011; 40: 913
• 8 James CA, Coelho AL, Gevaert M, Forgione P, Snieckus V. J. Org. Chem. 2009; 74: 4094
• 9a Zhao YL, Li Y, Li Y, Gao LX, Han FS. Chem. Eur. J. 2010; 16: 4991
• 9b Chen H, Huang ZB, Hu XM, Tang G, Xu PX, Zhao YF, Cheng CH. J. Org. Chem. 2011; 76: 2338
• 9c Liu L, Zhang S, Chen H, Lv Y, Zhu J, Zhao Y. Chem. Asian J. 2013; 8: 2592
• 10a Tang ZY, Hu QS. J. Am. Chem. Soc. 2004; 126: 3058
• 10b Wilson DA, Wilson CJ, Rosen BM, Percec V. Org. Lett. 2008; 10: 4879
• 10c LaBerge NA, Love JA. Eur. J. Org. Chem. 2015; 5546
• 10d Niwa T, Ochiai H, Watanabe Y, Hosoya T. J. Am. Chem. Soc. 2015; 137: 14313
• 10e Hansen AL, Ebran J.-P, Gøgsig TM, Skrydstrup T. Chem. Commun. 2006; 4137
• 10f Dürr AB, Yin G, Kalvet I, Napoly F, Schoenebeck F. Chem. Sci. 2016; 1076
• 10g Yu D, Wang C, Yao C, Shen Q, Lu L. Org. Lett. 2014; 16: 5544
• 11 Molander GA, Beaumard F. Org. Lett. 2010; 12: 4022
• 12a Leowanawat P, Zhang N, Resmerita A.-M, Rosen BM, Percec V. J. Org. Chem. 2011; 76: 9946
• 12b Leowanawat P, Zhang N, Percec V. J. Org. Chem. 2012; 77: 1018
• 13a Tobisu M, Shimasaki T, Chatani N. Angew. Chem. Int. Ed. 2008; 47: 4866
• 13b Zarate C, Manzano R, Martin R. J. Am. Chem. Soc. 2015; 137: 6754
• 14 Leowanawat P, Zhang N, Safi M, Hoffman DJ, Fryberger MC, George A, Percec V. J. Org. Chem. 2012; 77: 2885
• 15a Xing C.-H, Lee J.-R, Tang Z.-Y, Zheng JR, Hu Q.-S. Adv. Synth. Catal. 2011; 353: 2051
• 15b Hu F, Lei X. Tetrahedron 2014; 70: 3854
• 15c Fan X.-H, Yang L.-M. Eur. J. Org. Chem. 2010; 2457
• 16 Jezorek RL, Zhang N, Leowanawat P, Bunner MH, Gutsche N, Pesti AK. R, Olsen JT, Percec V. Org. Lett. 2014; 16: 6326
• 17 Malineni J, Jezorek RL, Zhang N, Percec V. Synthesis 2016; 48, in press; DOI: 10.1055/s-0035-1562342
• 18a Gao H, Li Y, Zhou Y.-G, Han F.-S, Lin Y.-J. Adv. Synth. Catal. 2011; 353: 309
• 18b Zhao Y.-L, Li Y, Li S.-M, Zhou Y.-G, Sun F.-Y, Gao L.-X, Han F.-S. Adv. Synth. Catal. 2011; 353: 1543
• 19a Percec V, Bae JY, Zhao MY, Hill DH. J. Org. Chem. 1995; 60: 176
• 19b Percec V, Okita S, Weiss R. Macromolecules 1992; 25: 1816
• 19c Percec V, Okita S. J. Polym. Sci., Part A: Polym. Chem. 1993; 31: 877
• 19d Percec V, Okita S. J. Polym. Sci., Part A: Polym. Chem. 1993; 31: 1087
• 19e Percec V, Bae JY, Zhao MY, Hill DH. Macromolecules 1995; 28: 6726
• 19f Grob MC, Feiring AE, Auman BC, Percec V, Zhao MY, Hill DH. Macromolecules 1996; 29: 7284
• 19g Percec V, Zhao MY, Bae JY, Hill DH. Macromolecules 1996; 29: 3727
• 19h Percec V, Asandei AD, Hill DH, Crawford D. Macromolecules 1999; 32: 2597
• 20a Rosen BM, Huang C, Percec V. Org. Lett. 2008; 10: 2597
• 20b Moldoveanu C, Wilson DA, Wilson CJ, Corcoran P, Rosen BM, Percec V. Org. Lett. 2009; 11: 4974
• 20c Moldoveanu C, Wilson DA, Wilson CJ, Leowanawat P, Resmerita A.-M, Liu C, Rosen BM, Percec V. J. Org. Chem. 2010; 75: 5438
• 20d Leowanawat P, Resmerita A.-M, Moldoveanu C, Liu C, Zhang N, Wilson DA, Hoang LM, Rosen BM, Percec V. J. Org. Chem. 2010; 75: 7822
• 20e Wilson DA, Wilson CJ, Moldoveanu C, Resmerita A.-M, Corcoran P, Hoang LM, Rosen BM, Percec V. J. Am. Chem. Soc. 2010; 132: 1800
• 21 Molander GA, Ellis N. Acc. Chem. Res. 2007; 40: 275
• 22 Harris MR, Hanna LE, Greene MA, Moore CE, Jarvo ER. J. Am. Chem. Soc. 2013; 135: 3303
• 23a Cassar L. J. Organomet. Chem. 1973; 54: C57
• 23b Cassar L, Ferrara S, Foa M. Adv. Chem. Ser. 1974; 252
• 23c Foa M, Cassar L. J. Chem. Soc., Dalton Trans. 1975; 2572
• 23d Vansoolingen J, Verkruijsse HD, Keegstra MA, Brandsma L. Synth. Commun. 1990; 20: 3153
• 24 Zhang N, Hoffman DJ, Gutsche N, Gupta J, Percec V. J. Org. Chem. 2012; 77: 5956
• 25a Lei X, Obregon KA, Alla J. Appl. Organomet. Chem. 2013; 27: 419
• 25b Standley EA, Jamison TF. J. Am. Chem. Soc. 2013; 135: 1585
• 25c Chen C, Yang L.-M. Tetrahedron Lett. 2007; 48: 2427
• 25d Zheng X, Yang Q, Li Z, Zhu Z, Cui X, Fu H, Chen H, Li R. Catal. Commun. 2014; 57: 143
• 25e Christian AH, Mueller P, Monfette S. Organometallics 2014; 33: 2134
• 25f Magano J, Monfette S. ACS Catal. 2015; 5: 3120
• 25g Ge S, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 12837
• 25h Graham TJ. A, Doyle AG. Org. Lett. 2012; 14: 1616
• 26a Park NH, Teverovskiy G, Buchwald SL. Org. Lett. 2014; 16: 220
• 26b Chen C, Yang L.-M. J. Org. Chem. 2007; 72: 6324