Synthesis of Substituted Benzils from Diarylalkyne Oxidation

Abstract

In this review, the oxidation of diarylalkynes leading to functionalized benzils [di(het)aryl 1,2-diketones] is summarized. Some synthetic one-pot transformations of internal arylalkynes leading to the construction of heterocycles are presented.

1 Introduction

2 Oxidation Using Inorganic Reagents

2.1 I₂, I⁺, and NIS

2.2 Potassium Permanganate (KMnO₄)

2.3 Sulfur Trioxide (SO₃)

2.4 Potassium Peroxymonosulfate (Oxone)

2.5 O₂, hν, MgBr₂·Et₂O

2.6 Cerium Ammonium Nitrate (CAN)

2.7 Overview of Inorganic Reagents

3 Metal-Catalyzed Oxidation of Diarylalkynes

3.1 Palladium Catalysts

3.2 Copper Catalysts

3.3 Iron Catalysts

3.4 Ruthenium Catalysts

3.5 Gold Catalysts

3.6 Mercury Catalysts

3.7 Overview of Metal Catalysts

4 Sequential Hydration–Oxidation of Diarylalkynes

5 Applications to the Synthesis of Heterocycles

5.1 One-Pot Access to Heterocycles

5.2 Access to Various Heterocycles

6 Conclusions

Key words

alkynes - catalysis - heterocycles - ketones - oxidation - palladium

• References


For selected examples see:
• 1a Mahabusarakam W, Deachathai S, Phongpaichit S, Jansakul C, Taylor WC. Phytochemistry 2004; 65: 1185
• 1b Johns SR, Lambenon JA, Sioum AA, Willing RJ. Aust. J. Chem. 1970; 23: 353
• 1c Rodrigo RG. A, Manrke RH. F, Holland HL, MacLean DB. Can. J. Chem. 1976; 54: 471
• 1d Re L, Maurer B, Ohloff G. Helv. Chim. Acta 1973; 56: 1882
• 1e Angelstro MR, Mehdi S, Burkhart JP, Peet NP, Bey P. J. Med. Chem. 1990; 33: 11
• 1f Nicolaou KC, Gray DL. F, Tae J. J. Am. Chem. Soc. 2004; 126: 613
• 1g Wadkins RM, Hyatt JL, Wei X, Yoon KJ. P, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM. J. Med. Chem. 2005; 48: 2906
• 2a Mousset C, Giraud A, Provot O, Hamze A, Bignon J, Liu JM, Thoret S, Dubois J, Brion J.-D, Alami M. Bioorg. Med. Chem. Lett. 2008; 18: 3266
• 2b Ganapaty S, Srilakshmi GV. K, Pannakal ST, Rahman H, Laatsch H, Brun R. Phytochemistry 2009; 70: 95
• 2c Al-kahraman YM. S. A, Yasinzai M, Singh GS. Arch. Pharmacal. Res. 2012; 35: 1009
• 3 Harada Y, Nakagawa Y, Wadkins RM, Potter PM. Bioorg. Med. Chem. 2009; 17: 149
• 4a Kósa C, Lukáč I, Weiss RG. Macromolecules 2000; 33: 4015
• 4b Mosnáček J, Weiss RG, Lukáč I. Macromolecules 2002; 35: 3870
• 4c Mosnáček J, Weiss RG, Lukáč I. Macromolecules 2004; 37: 1304
• 4d Corrales T, Catalina F, Peinando C, Allen NS. J. Photochem. Photobiol. 2003; 159: 103
• 5 Ita BI, Offiong OE. Mater. Chem. Phys. 2001; 70: 330

For selected exemples see:
• 6a Mousset C, Provot O, Hamze A, Bignon J, Brion J.-D, Alami M. Tetrahedron 2008; 64: 4287
• 6b Xu Y, Wan X. Tetrahedron Lett. 2013; 54: 642
• 6c Wolkenberg SE, Wisnoski DD, Leister WH, Wang Y, Zhao Z, Lindsley CW. Org. Lett. 2004; 6: 1453
• 6d McKenna JM, Halley F, Souness JE, McLay IM, Pickett SD, Collis AJ, Page K, Ahmed I. J. Med. Chem. 2002; 45: 2173
• 6e Herrera AJ, Rondón M, Suárez E. J. Org. Chem. 2008; 73: 3384
• 7a Clarke HT, Dreger EE. Org. Synth. Coll. Vol. I . John Wiley & Sons; London: 1941: 87
• 7b Rigby WJ. J. Chem. Soc. 1951; 793
• 7c Fieser LF, Fieser M. Reagents for Organic Synthesis . Vol. 1. Wiley; New York: 1967: 1
• 7d McKillop A, Swann B, Ford ME, Taylor EC. J. Am. Chem. Soc. 1973; 95: 3641
• 7e Zhang G.-S, Shi Q.-Z, Chen M.-F, Cai K. Synth. Commun. 1997; 27: 953
• 7f Okimoto M, Takahashi Y, Nagata Y, Sasaki G, Numata K. Synthesis 2005; 705
• 8a Khurana JM, Kandpal BM. Tetrahedron Lett. 2003; 44: 4909
• 8b Anelli PL, Banfi S, Montanari F, Quici S. J. Org. Chem. 1989; 54: 2970
• 8c Iwahama T, Sakaguchi S, Nishiyama Y, Ishii Y. Tetrahedron Lett. 1995; 36: 6923

For selected examples of oxidation of diphenylacetylene, see:
• 9a Wolfe S, Pilgrim WR, Garrard TF, Chamberlain P. Can. J. Chem. 1971; 49: 1099
• 9b Lee DG, Chang VS. Synthesis 1978; 462
• 9c Sheats WB, Olli LK, Stout R, Lundeen JT, Justus R, Nigh WG. J. Org. Chem. 1979; 44: 4075
• 9d Gebeyehu G, McNelis E. J. Org. Chem. 1980; 45: 4280
• 9e Müller P, Godoy J. Helv. Chim. Acta 1981; 64: 2531
• 9f Wolfe S, Ingold CF. J. Am. Chem. Soc. 1983; 105: 7755
• 9g Firouzabadi H, Sardarian AR. Synthesis 1985; 946
• 9h Ballistreri FP, Failla S, Tomaselli GA, Curci R. Tetrahedron Lett. 1986; 27: 5139
• 9i Firouzabadi H, Sardarian AR, Moosavipour H, Afshari GM. Synthesis 1986; 285
• 9j Baskaran S, Das J, Chandrasekaran S. J. Org. Chem. 1989; 54: 5182
• 9k Zhu Z, Espenson JH. J. Org. Chem. 1995; 60: 7728
• 9l Clayton MD, Marcinow Z, Rabideau PW. Tetrahedron Lett. 1998; 39: 9127
• 9m Li P, Cheong FH, Chao LC. F, Lin YH, Williams ID. J. Mol. Catal. A: Chem. 1999; 145: 111
• 9n Che CM, Yu WY, Chan PM, Cheng WC, Peng SM, Lau KC, Li WK. J. Am. Chem. Soc. 2000; 122: 11380
• 9o Kobayashi S, Miyamura H, Akiyama R, Ishida T. J. Am. Chem. Soc. 2005; 127: 9251
• 9p Daw P, Petakamsetty R, Sarbajna A, Laha S, Ramapanicker R, Bera JK. J. Am. Chem. Soc. 2014; 136: 13987
• 10 Yubusov MS, Filimonov VD. Synthesis 1991; 131
• 11 Yusubov MS, Filimonov VD, Vasilyeva VP, Chi K.-W. Synthesis 1995; 1234
• 12 Foster EJ, Babuin J, Nguyen N, Williams VE. Chem. Commun. 2004; 2052
• 13 Sakthivel K, Srinivasan K. Eur. J. Org. Chem. 2011; 2781
• 14 Sakthivel K, Srinivasan K. Eur. J. Org. Chem. 2013; 3386
• 15 Tingoli M, Mazzella M, Panunzi B, Tuzi A. Eur. J. Org. Chem. 2011; 399
• 16 Chen C.-Y, Hu W.-P, Liu M.-C, Yan P.-C, Wang J.-J, Chung M.-I. Tetrahedron 2013; 69: 9735
• 17 Niu M, Fu H, Jiang Y, Zhao Y. Synthesis 2008; 2879
• 18 Chikugo T, Yauchi Y, Ide M, Iwasawa T. Tetrahedron 2014; 70: 3988
• 19 Srinavasan NS, Lee DG. J. Org. Chem. 1979; 44: 1574
• 20 Trosien S, Waldvogel SR. Org. Lett. 2012; 14: 2976
• 21 Walsh CJ, Mandal BK. J. Org. Chem. 1999; 64: 6102
• 22 Deng X, Mani NS. Org. Lett. 2006; 8: 269
• 23 Rogatchov VO, Filimonov VD, Yusubov MS. Synthesis 2001; 1001
• 24 Chen Y.-J, Wu M.-J. Synthesis 2009; 2155
• 25 Stille JK, Whitehurst DD. J. Am. Chem. Soc. 1964; 86: 4871
• 26 Nobuta T, Tada N, Hattori K, Hirashima S.-i, Miura T, Itoh A. Tetrahedron Lett. 2011; 52: 875
• 27 Fu C.-F, Hu W.-P, Vandavasi JK, Liao C.-C, Hung C.-Y, Wang J.-J. Synlett 2012; 23: 2132
• 28 Muzard J. J. Mol. Catal. A: Chem. 2011; 338: 7
• 29 Mori S, Takubo M, Yanase T, Maegawa T, Monguchi Y, Sajiki H. Adv. Synth. Catal. 2010; 352: 1630
• 30 Sawama Y, Takubo M, Mori S, Monguchi Y, Sajiki H. Eur. J. Org. Chem. 2011; 3361
• 31 Gao A, Yang F, Li J, Wu Y. Tetrahedron 2012; 68: 4950
• 32 Ren W, Xia Y, Ji SJ, Zhang Y, Wan X, Zhao J. Org. Lett. 2009; 11: 1841
• 33 Byun S, Chung J, Lim T, Kwon J, Kim BM. RCS Adv. 2014; 4: 34084
• 34 Chandrasekhar S, Reddy NK, Kumar VP. Tetrahedron Lett. 2010; 51: 3623
• 35 Chi KW, Yusubov MS, Filimonov VD. Synth. Commun. 1994; 24: 2119
• 36 Yusubov MS, Zholobova GA, Vasilevsky SF, Tretyakov EV, Knight DW. Tetrahedron 2002; 58: 1607
• 37 Zhang W, Zhang J, Liu Y, Xu Z. Synlett 2013; 24: 2709
• 38 Banks RE, Lawrence NJ, Popplewell AL. Synlett 1994; 831
• 39 Xu N, Gu DW, Dong YS, Yi FP, Cai L, Wu XY, Guo XX. Tetrahedron Lett. 2015; 56: 1517
• 40 Min H, Palani T, Park K, Hwang J, Lee S. J. Org. Chem. 2014; 79: 6279
• 41 Xia XF, Gu Z, Liu W, Wang N, Wang H, Xia Y, Gao H, Liu X. Org. Biomol. Chem. 2014; 12: 9909
• 42 Giraud A, Provot O, Peyrat JF, Alami M, Brion JD. Tetrahedron 2006; 62: 7667
• 43 Enthaler S. ChemCatChem 2011; 3: 1929
• 44 Ren W, Liu J, Chen L, Wan X. Adv. Synth. Catal. 2010; 352: 1424
• 45 Tummatorn J, Khorphueng P, Petsom A, Muangsin N, Chaichit N, Roengsumran S. Tetrahedron 2007; 63: 11878
• 46 Miao Y, Dupé A, Bruneau C, Fischmeister C. Eur. J. Org. Chem. 2014; 5071
• 47 Xu CF, Xu M, Jia YX, Li CY. Org. Lett. 2011; 13: 1556
• 48 Liu Y, Chen X, Zhang J, Xu Z. Synlett 2013; 24: 1371
• 49 Kucherov M. Ber. Dtsch. Chem. Ges. 1881; 14: 1540
• 50 Jung ME, Deng G. Org. Lett. 2014; 16: 2142
• 51 Wan Z, Jones CD, Mitchell D, Pu JY, Zhang TY. J. Org. Chem. 2006; 71: 826
• 52 He W, Meyers MR, Hanney B, Spada A, Bilder G, Galzcinski H, Amin D, Needle S, Page K, Jayyosi Z, Perrone H. Bioorg. Med. Chem. Lett. 2003; 13: 3097
• 53 Kim YB, Kim YH, Park JY, Kim SK. Bioorg. Med. Chem. Lett. 2004; 14: 541
• 54 Zhao Z, Winnoski DD, Wolkenberg SE, Leister WH, Wang Y, Lindsley CW. Tetrahedron Lett. 2004; 45: 4873
• 55 Girish YR, Kumar SS, Thimmaiah KN, Rangappa KS, Shashikanth S. RSC Adv. 2015; 5: 75533
• 56 Hinsberg O. Ber. Dtsch. Chem. Ges. 1912; 45: 2413
• 57 Traversone A, Brill WK.-D. Tetrahedron Lett. 2007; 48: 3535
• 58 Dahra D, Gayen KS, Khamarui S, Pandit P, Ghosh S, Maiti DK. J. Org. Chem. 2012; 77: 10441
• 59 Nongkhlaw RL, Nongrum R, Myrboh B. Heterocycl. Commun. 2003; 9: 365
• 60 Zhao Z, Leister WH, Strauss KA, Wisnoski DD, Lindsley CW. Tetrahedron Lett. 2003; 44: 1123
• 61 Brown RK. Indoles, Part 1 . In The Chemistry of Heterocyclic Compounds . Vol 25. Houlihan WI. Wiley; New York: 1972: 227
• 62 Cabrera A, Sharma P, Ayala M, Rubio-Perez L, Amézquita-Valencia M. Tetrahedron Lett. 2011; 52: 6758
• 63 Vuong TM. H, Bui T.-T, Sournia-Saquet A, Moreau A, Moineau-Chane Ching KI. Inorg. Chem. 2014; 53: 2841