26.13 Product Class 13: α-Aryl and α-Hetaryl Ketones

Abstract

This chapter outlines many of the methods used to synthesize α-aryl ketones and α-hetaryl ketones. Attention is focused on transition-metal-catalyzed cross-coupling reactions of (het)aryl halides and pseudohalides with ketones and ketone derivatives, which are particularly useful for enantioselective synthesis, but other methods such as nucleophilic aromatic substitutions are also discussed.

Key words

α-aryl ketones - α-hetaryl ketones - nucleophilic substitution - transition-metal catalysis - cross-coupling reactions - monophosphines - bisphosphines - N-heterocyclic carbenes - enantioselectivity - C—C bond formation

• 1 Snow RJ, Butz T, Hammach A, Kapadia S, Morwick TM, Prokopowicz III AS, Takahashi H, Tan JD, Tschantz MA, Wang X.-J. Tetrahedron Lett. 2002; 43: 7553

• 2 Prüger B, Hofmeister GE, Jacobsen CB, Alberg DG, Nielsen M, Jørgensen KA. Chem.–Eur. J. 2010; 16: 3783

• 3 Rossi RA, Bunnett JF. J. Am. Chem. Soc. 1972; 94: 683

• 4 Rossi RA, Bunnett JF. J. Org. Chem. 1973; 38: 1407

• 5 Bunnett JF, Sundberg JE. Chem. Pharm. Bull. 1975; 23: 2620

• 6 Bunnett JF, Gloor BF. Heterocycles 1976; 5: 377

• 7 Komin AP, Wolfe JF. J. Org. Chem. 1977; 42: 2481

• 8 Carver DR, Komin AP, Hubbard JS, Wolfe JF. J. Org. Chem. 1981; 46: 294

• 9 Hay JV, Wolfe JF. J. Am. Chem. Soc. 1975; 97: 3702

• 10 Semmelhack MF, Bargar TM. J. Am. Chem. Soc. 1980; 102: 7765

• 11 Borsky GL, Pierini AB, Rossi RA. J. Org. Chem. 1992; 57: 247

• 12 Galli C, Gentili P. J. Chem. Soc., Perkin Trans. 2 1993; 1135

• 13 Nazareno MA, Rossi RA. Tetrahedron Lett. 1994; 35: 5185

• 14 Rossi RA, Bunnett JF. J. Org. Chem. 1973; 38: 3020

• 15 Semmelhack MF, Bargar TM. J. Org. Chem. 1977; 42: 1481

• 16 Gustavino JF, Rossi RA. J. Org. Chem. 2012; 77: 460

• 17 Fox JM, Huang X, Chieffi A, Buchwald SL. J. Am. Chem. Soc. 2000; 122: 1360

• 18 Kawatsura M, Hartwig JF. J. Am. Chem. Soc. 1999; 121: 1473

• 19 Guo Y, Twamley B, Shreeve JM. Org. Biomol. Chem. 2009; 7: 1716

• 20 Satoh T, Kametani Y, Terao Y, Miura M, Nomura M. Tetrahedron Lett. 1999; 40: 5345

• 21 Churruca F, SanMartin R, Tellitu I, Domínguez E. Org. Lett. 2002; 4: 1591

• 22 Churruca F, SanMartin R, Carril M, Tellitu I, Domínguez E. Tetrahedron 2004; 60: 2393

• 23 Ehrentraut A, Zapf A, Beller M. Adv. Synth. Catal. 2002; 344: 209

• 24 Rutherford JL, Rainka MP, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 15 168

• 25 Biscoe MR, Buchwald SL. Org. Lett. 2009; 11: 1773

• 26 Ackermann L, Spatz JH, Gschrei CJ, Born R, Althammer A. Angew. Chem. Int. Ed. 2006; 45: 7627

• 27 Hesp KD, Lundgren RJ, Stradiotto M. J. Am. Chem. Soc. 2011; 133: 5194

• 28 Palucki M, Buchwald SL. J. Am. Chem. Soc. 1997; 119: 11 108

• 29 Limbeck M, Wamhoff H, Rölle T, Griebenow N. Tetrahedron Lett. 2006; 47: 2945

• 30 Carril M, SanMartin R, Churruca F, Tellitu I, Domínguez E. Org. Lett. 2005; 7: 4787

• 31 Desai LV, Ren DT, Rosner T. Org. Lett. 2010; 12: 1032

• 32 Hamann BC, Hartwig JF. J. Am. Chem. Soc. 1997; 119: 12 382

• 33 Grasa GA, Colacot TJ. Org. Lett. 2007; 9: 5489

• 34 Grasa GA, Colacot TJ. Org. Process Res. Dev. 2008; 12: 522

• 35 Churruca F, SanMartin R, Tellitu I, Domínguez E. Tetrahedron Lett. 2006; 47: 3233

• 36 Viciu MS, Germaneau RF, Nolan SP. Org. Lett. 2002; 4: 4053

• 37 Viciu MS, Germaneau RF, Navarro-Fernandez O, Stevens ED, Nolan SP. Organometallics 2002; 21: 5470

• 38 Singh R, Nolan SP. J. Organomet. Chem. 2005; 690: 5832

• 39 Viciu MS, Kelly III RA, Stevens ED, Naud F, Studer M, Nolan SP. Org. Lett. 2003; 5: 1479

• 40 Navarro O, Marion N, Oonishi Y, Kelly III RA, Nolan SP. J. Org. Chem. 2006; 71: 685

• 41 Navarro O, Marion N, Scott NM, González J, Amoroso D, Bell A, Nolan SP. Tetrahedron 2005; 61: 9716

• 42 Marion N, Ecarnot EC, Navarro O, Amoroso D, Bell A, Nolan SP. J. Org. Chem. 2006; 71: 3816

• 43 Cao C, Wang L, Cai Z, Zhang L, Guo J, Pang G, Shi Y. Eur. J. Org. Chem. 2011; 1570

• 44 Xiao Z.-K, Shao L.-X. Synthesis 2012; 44: 711

• 45 Lavallo V, Canac Y, Präsang C, Donnadieu B, Bertrand G. Angew. Chem. Int. Ed. 2005; 44: 5705

• 46 Åhman J, Wolfe JP, Troutman MV, Palucki M, Buchwald SL. J. Am. Chem. Soc. 1998; 120: 1918

• 47 Hamada T, Chieffi A, Åhman J, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 1261

• 48 Laio X, Weng Z, Hartwig JF. J. Am. Chem. Soc. 2008; 130: 195

• 49 Richter C, Ranganath KVS, Glorius F. Adv. Synth. Catal. 2012; 354: 377

• 50 Matsubara K, Ueno K, Koga Y, Hara K. J. Org. Chem. 2007; 72: 5069

• 51 Chen G, Kwong FW, Chan HO, Yu W.-Y, Chan ASC. Chem. Commun. (Cambridge) 2006; 1413

• 52 Ge S, Hartwig JF. J. Am. Chem. Soc. 2011; 133: 16 330

• 53 He C, Guo S, Huang L, Lei A. J. Am. Chem. Soc. 2010; 132: 8273

• 54 Fraboni A, Fagnoni M, Albini A. J. Org. Chem. 2003; 68: 4386

• 55 Kuwajima I, Urabe H. J. Am. Chem. Soc. 1982; 104: 6831

• 56 Iwama T, Rawal VH. Org. Lett. 2006; 8: 5725

• 57 Guo Y, Shreeve JM. Chem. Commun. (Cambridge) 2007; 3583

• 58 Su W, Raders S, Verkade JG, Liao X, Hartwig JF. Angew. Chem. Int. Ed. 2006; 45: 5852

• 59 Chobanian HR, Liu P, Chioda MD, Guo Y, Lin LS. Tetrahedron Lett. 2007; 48: 1213

• 60 Chae J, Yun J, Buchwald SL. Org. Lett. 2004; 6: 4809

• 61 Nilsson P, Larhed M, Halberg A. J. Am. Chem. Soc. 2003; 125: 3430

• 62 Datta GK, Nordemann P, Dackenberg J, Nilsson P, Halberg A, Larhed M. Tetrahedron: Asymmetry 2008; 19: 1120

• 63 Datta GK, Larhed M. Org. Biomol. Chem. 2008; 6: 674

• 64 Saito R, Izumi T, Kasahara A. Bull. Chem. Soc. Jpn. 1973; 46: 1776

• 65 Kosugi M, Suzuki M, Hagiwara I, Goto K, Saitoh K, Migita T. Chem. Lett. 1982; 939

• 66 Kosugi M, Hagiwara I, Sumiya T, Migita T. J. Chem. Soc., Chem. Commun. 1983; 344

• 67 Kosugi M, Hagiwara I, Sumiya T, Migita T. Bull. Chem. Soc. Jpn. 1984; 57: 242

• 68 Liu P, Lanza Jr TJ, Jewell JP, Jones CP, Hagmann WK, Lin LS. Tetrahedron Lett. 2003; 44: 8869

• 69 Nguyen HN, Huang X, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 11 818

• 70 Ackermann L, Mehta VP. Chem.–Eur. J. 2012; 18: 10 230

• 71 Molinaro C, Mowat J, Gosselin F, O’Shea PD, Marcoux J.-F, Angelaud R, Davies IW. J. Org. Chem. 2007; 72: 1856

• 72 Hering T, Hari P, König B. J. Org. Chem. 2012; 77: 10 347

• 73 Brown HC, Nambu H, Rogic MM. J. Am. Chem. Soc. 1969; 91: 6852

• 74 Liu C, He C, Shi W, Chen M, Lei A. Org. Lett. 2007; 9: 5601

• 75 Wu X.-F, Neumann H, Beller M. Tetrahedron Lett. 2010; 51: 6146

• 76 Wu X.-F, Neumann H, Beller M. Adv. Synth. Catal. 2011; 353: 788

• 77 Barton DHR, Blazejewski J.-C, Charpiot B, Finet J.-P, Motherwell WB, Barros Papoula MT, Stanforth SP. J. Chem. Soc., Perkin Trans. 1 1985; 2667

• 78 Moskalev N, Barbasiewicz M, Mąkosza M. Tetrahedron 2004; 60: 347

• 79 Hamana M, Iwasaki G, Saeki S. Heterocycles 1982; 17: 177

• 80 Gallardo I, Guirado G, Marquet J. Eur. J. Org. Chem. 2002; 261

• 81 Bujok R, Wróbel Z, Wojciechowski K. Synlett 2012; 23: 1315