Synthesis 2020; 52(04): 565-573
DOI: 10.1055/s-0039-1690045
paper
© Georg Thieme Verlag Stuttgart · New York

Nickel versus Palladium in Cross-Coupling Catalysis: On the Role of Substrate Coordination to Zerovalent Metal Complexes

Alasdair K. Cooper
a  WestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, Scotland   Email: [email protected]
,
Paul M. Burton
b  Syngenta, Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, UK
,
David J. Nelson
a  WestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, Scotland   Email: [email protected]
› Author Affiliations
We thank Syngenta and the Engineering and Physical Sciences Research Council for an Industrial CASE Studentship for AKC (EP/P51066X/1), and the University of Strathclyde for a Chancellor’s Fellowship for DJN (2014–18). We are grateful to the Carnegie Trust for the Universities of Scotland for a Research Incentive Grant (RIG008165).
Further Information

Publication History

Received: 17 November 2019

Accepted after revision: 16 December 2019

Publication Date:
19 December 2019 (online)


Dedicated to Gavin Bain on the occasion of his retirement, in acknowledgement of his many years of service within the Department of Pure and Applied Chemistry at the University of Strathclyde.

Published as part of the Bürgenstock Special Section 2019 Future Stars in Organic Chemistry

Abstract

A detailed comparison of the effect of coordinating functional groups on the performance of Suzuki–Miyaura reactions catalysed by nickel and palladium is reported, using competition experiments, robustness screening, and density functional theory calculations. Nickel can interact with a variety of functional groups, which manifests as selectivity in competitive cross-coupling reactions. The presence of these functional groups on exogenous additives has effects on cross-coupling reactions that range from a slight improvement in yield to the complete cessation of the reaction. In contrast, palladium does not interact sufficiently strongly with these functional groups to induce selectivity in cross-coupling reactions; the selectivity of palladium-catalysed cross-coupling reactions is predominantly governed by aryl halide electronic properties.

Supporting Information

 
  • References

  • 1 Negishi E.-i. Angew. Chem. Int. Ed. 2011; 50: 6738
  • 2 Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6722
  • 3 Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
  • 4 Cooper A, Leonard D, Bajo S, Burton P, Nelson D. ChemRxiv 2019; preprint; DOI DOI: 10.26434/chemrxiv.773716.v1.
  • 5 Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509(7500): 299
  • 6 Ananikov VP. ACS Catal. 2015; 5: 1964
  • 7 Bajo S, Laidlaw G, Kennedy AR, Sproules S, Nelson DJ. Organometallics 2017; 36: 1662
  • 8 Guard LM, Mohadjer Beromi M, Brudvig GW, Hazari N, Vinyard DJ. Angew. Chem. Int. Ed. 2015; 54: 13352
  • 9 Zhang K, Conda-Sheridan MR, Cooke S, Louie J. Organometallics 2011; 30: 2546
  • 10 Tsou TT, Kochi JK. J. Am. Chem. Soc. 1979; 101: 6319
  • 11 Nelson DJ, Maseras F. Chem. Commun. 2018; 54: 10646
  • 12 Funes-Ardoiz I, Nelson DJ, Maseras F. Chem. Eur. J. 2017; 23: 16728
  • 13 West MJ, Watson AJ. B. Org. Biomol. Chem. 2019; 17: 5055
  • 14 Collins KD, Glorius F. Nat. Chem. 2013; 5: 597
  • 15 Hansch C, Leo A, Taft RW. Chem. Rev. 1991; 91: 165
  • 16 Portnoy M, Milstein D. Organometallics 1993; 12: 1665
  • 17 Christian AH, Müller P, Monfette S. Organometallics 2014; 33: 2134
  • 18 Payard PA, Perego LA, Ciofini I, Grimaud L. ACS Catal. 2018; 8: 4812
  • 19 Strawser D, Karton A, Zenkina OV, Iron MA, Shimon LJ. W, Martin JM. L, van der Boom ME. J. Am. Chem. Soc. 2005; 127: 9322
  • 20 Zenkina OV, Karton A, Freeman D, Shimon LJ. W, Martin JM. L, van der Boom ME. Inorg. Chem. 2008; 47: 5114
  • 21 Zenkina OV, Gidron O, Shimon LJ. W, Iron MA, van der Boom ME. Chem. Eur. J. 2015; 21: 16113
  • 22 Orbach M, Shankar S, Zenkina OV, Milko P, Diskin-Posner Y, van der Boom ME. Organometallics 2015; 34: 1098
  • 23 He W, Patrick BO, Kennepohl P. Nat. Commun. 2018; 9: 3866
  • 24 Rothstein PE, Comanescu CC, Iluc VM. Chem. Eur. J. 2017; 23: 16948
  • 25 Tejel C, Asensio L, del Río MP, de Bruin B, López JA, Ciriano MA. Angew. Chem. Int. Ed. 2011; 50: 8839
  • 26 Desnoyer AN, He W, Behyan S, Chiu W, Love JA, Kennepohl P. Chemistry 2019; 25: 5259
  • 27 He W, Kennepohl P. Faraday Discuss. 2019; 220: 133
  • 28 Kozuch S, Shaik S. Acc. Chem. Res. 2011; 44: 101
  • 29 Standley EA, Smith SJ, Müller P, Jamison TF. Organometallics 2014; 33: 2012
  • 30 McIntyre J, Mayoral-Soler I, Salvador P, Poater A, Nelson DJ. Catal. Sci. Technol. 2018; 8: 3174
  • 31 Fulmer GR, Miller AJ. M, Sherden NH, Gottlieb HE, Nudelman A, Stoltz BM, Bercaw JE, Goldberg KI. Organometallics 2010; 29: 2176
  • 32 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision D.01 . Gaussian, Inc; Wallingford CT: 2009
  • 33 Fey N, Ridgway BM, Jover J, McMullin CL, Harvey JN. Dalton Trans. 2011; 40: 11184
  • 34 Yuan Y, Shi X, Liu W. Synlett 2011; 559
  • 35 Tobisu M, Xu T, Shimasaki T, Chatani N. J. Am. Chem. Soc. 2011; 133: 19505
  • 36 Kim D.-S, Ham J. Org. Lett. 2010; 12: 1092
  • 37 Yu D.-G, Yu M, Guan B.-T, Li B.-J, Zheng Y, Wu Z.-H, Shi Z.-J. Org. Lett. 2009; 11: 3374
  • 38 Dubost E, Fossey C, Cailly T, Rault S, Fabis F. J. Org. Chem. 2011; 76: 6414
  • 39 Bandari R, Höche T, Prager A, Dirnberger K, Buchmeiser MR. Chem. Eur. J. 2010; 16: 4650