1.1.3 Rhodium/Palladium Dual Catalysis

U B. Kim; S.-g. Lee

Abstract

This chapter reviews the development and applications of rhodium/palladium dual catalysis in organic synthesis. Dual catalysis can be broadly classified into two types: (1) Synergistic dual catalysis, where two independent rhodium and palladium catalytic cycles operate simultaneously to activate two different starting materials with balanced kinetics to afford two catalytically activated intermediates. These activated intermediates react with each other to afford the final product. (2) Orthogonal tandem dual catalysis, where two catalytic cycles operate in a sequential manner, one after the other, to promote two or more mechanistically distinct reaction steps in a single pot to furnish the product. The first part of the chapter covers synergistic rhodium/palladium dual catalysis, detailing examples that feature a direct reaction between rhodium-activated intermediates and orthogonal, palladium-activated intermediates. The second part of the chapter describes one-pot reactions that utilize initial rhodium catalysis and sequential palladium catalysis. A single example where initial palladium catalysis is followed by subsequent rhodium catalysis is also presented.

Schlüsselwörter

dual catalysis - transition-metal catalysis - rhodium - palladium - synergistic catalysis - orthogonal tandem catalysis - π-allylpalladium(II) species - rhodium carbenoids - multicomponent reactions - heterocycle synthesis - one-pot reactions - allylation - carbonylation

• 1 Allen AE, MacMillan DWC. Chem. Sci. 2012; 3: 633

• 2 Lohr TL, Marks TJ. Nat. Chem. 2015; 7: 477

• 3 Pye DR, Mankad NP. Chem. Sci. 2017; 8: 1705

• 4 Lee JM, Na Y, Han H, Chang S. Chem. Soc. Rev. 2004; 33: 302

• 5 Lam H, Tsoung J, Lautens M. J. Org. Chem. 2017; 82: 6089

• 6 Panteleev J, Zhang L, Lautens M. Angew. Chem. Int. Ed. 2011; 50: 9089

• 7 Zhang L, Panteleev J, Lautens M. J. Org. Chem. 2014; 79: 12159

• 8 Sawamura M, Sudoh M, Ito Y. J. Am. Chem. Soc. 1996; 118: 3309

• 9 Sawamura M, Hamashima H, Ito Y. J. Am. Chem. Soc. 1992; 114: 8295

• 10 Nowicki A, Mortreux A, Agbossou-Niedercorn F. Tetrahedron: Asymmetry 2005; 16: 1295

• 11 Brennführer A, Neumann H, Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114

• 12 Baillargeon VP, Stille JK. J. Am. Chem. Soc. 1986; 108: 452

• 13 Ibrahim MYS, Denmark SE. Angew. Chem. Int. Ed. 2018; 57: 10362

• 14 Tsuji J, Shimizu I, Minami I, Ohashi Y, Sugiura T, Takahashi K. J. Org. Chem. 1985; 50: 1523

• 15 Chen Z.-S, Huang L.-Z, Jeon HJ, Xuan Z, Lee S.-g. ACS Catal. 2016; 6: 4914

• 16 Chen Z.-S, Huang X.-Y, Chen L.-H, Gao J.-M, Ji K. ACS Catal. 2017; 7: 7902

• 17 Chen Z.-S, Huang X.-Y, Gao J.-M, Ji K. Org. Lett. 2016; 18: 5876

• 18 Tsui GC, Tsoung J, Dougan P, Lautens M. Org. Lett. 2012; 14: 5542

• 19 Friedman AA, Panteleev J, Tsoung J, Huynh V, Lautens M. Angew. Chem. Int. Ed. 2013; 52: 9755

• 20 Zhang L, Qureshi Z, Sonaglia L, Lautens M. Angew. Chem. Int. Ed. 2014; 53: 13850

• 21 Tsoung J, Panteleev J, Tesch M, Lautens M. Org. Lett. 2014; 16: 110

• 22 Rebelo JM, Kress S, Friedman AA, Lautens M. Synthesis 2016; 48: 3155

• 23 Zhang L, Sonaglia L, Stacey J, Lautens M. Org. Lett. 2013; 15: 2128

• 24 Lied F, Brodnik Žugelj H, Kress S, Štefane B, Glorius F, Lautens M. ACS Catal. 2017; 7: 1378

• 25 Meng J, Fan L.-F, Han Z.-Y, Gong L.-Z. Chem 2018; 4: 1047

• 26 Heck RF, Breslow DS. J. Am. Chem. Soc. 1961; 83: 4023

• 27 Watkins AL, Landis CR. J. Am. Chem. Soc. 2010; 132: 10306

• 28 Dingwall P, Fuentes JA, Crawford L, Slawin AMZ, Bühl M, Clarke ML. J. Am. Chem. Soc. 2017; 139: 15921

• 29 Huang L.-Z, Xuan Z, Jeon HJ, Du Z.-T, Kim JH, Lee S.-g. ACS Catal. 2018; 8: 7340

• 30 Shen Y, Liu G, Zhou Z, Lu X. Org. Lett. 2013; 15: 3366

• 31 Xu H.-J, Lu Y, Farmer ME, Wang H.-W, Zhao D, Kang Y.-S, Sun W.-Y, Yu J.-Q. J. Am. Chem. Soc. 2017; 139: 2200

• 32 Mi R.-J, Sun Y.-Z, Wang J.-Y, Sun J, Xu Z, Zhou M.-D. Org. Lett. 2018; 20: 5126

• 33 Zhang S.-S, Wu J.-Q, Liu X, Wang H. ACS Catal. 2015; 5: 210

• 34 Jeong N, Seo SD, Shin JY. J. Am. Chem. Soc. 2000; 122: 10220

• 35 Trost BM, Malhotra S, Olson DE, Maruniak A, Du Bois J. J. Am. Chem. Soc. 2009; 131: 4190