When Alkyne π-Activation Meets Pinacol-Type [1,2]-Rearrangement: On the Invention of Domino Reactions for the Synthesis of Carbocycles and Heterocycles

Dedicated to Prof. Dr. Dr. h.c. Lutz F. Tietze, the inventor of ‘domino reactions’.

Abstract

This is a personal account on how to create domino re­actions consisting of catalyzed or uncatalyzed alkyne activation, ­cyclization, and subsequent rearrangement by a [1,2]-shift. In the context of literature reports on breakthrough works, we discuss our motivation, challenges, and success stories. The title reactions were developed with the goal of rapidly evolving molecular complexity in an experimentally easy manner. The value of the reactions in controlled syntheses of various carbocyclic and heterocyclic scaffolds through changing the nature of the substrate and the exact reaction conditions is demonstrated.

1 Introduction

2 Carbocyclizations

2.1 6-Endo Cyclization

2.2 6-Exo Cyclization

3 Heterocyclizations

4 Miscellaneous Reactions

5 Conclusions

Key words

domino reactions - rearrangements - catalysis - hetero­cycles - carbocycles

• References

• 1a Fittig R. Justus Liebigs Ann. Chem. 1859; 110: 23
• 1b Butlerov A. Justus Liebigs Ann. Chem. 1874; 174: 125
• 1c Berson JA. Angew. Chem. Int. Ed. 2002; 41: 1439
• 1d Kirsch SF. Nachr. Chem. 2008; 56: 1228

For selected applications in total synthesis, see:
• 2a Reisman SE, Ready JM, Hasuoka A, Smith CJ, Wood JL. J. Am. Chem. Soc. 2006; 128: 1448
• 2b Suzuki K, Takikawa H, Hachisu Y, Bode JW. Angew. Chem. Int. Ed. 2007; 46: 3252
• 2c Lebsack AD, Overman LE, Valentekovich RJ. J. Am. Chem. Soc. 2001; 123: 4851
• 2d Hirst GC, Johnson TO, Overman LE. J. Am. Chem. Soc. 1993; 115: 2992
• 2e Mulzer J, Greifenberg S, Buschmann J, Luger P. Angew. Chem., Int. Ed. Engl. 1993; 32: 1173
• 3 Tietze LF. Chem. Rev. 1996; 96: 115
• 4a Tietze LF, Brasche G, Gericke G. Domino Reactions in Organic Synthesis . Wiley-VCH; Weinheim: 2006
• 4b Pellisier H. Tetrahedron 2006; 62: 2143
• 4c Wasilke J.-C, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001
• 4d Kirsch SF. Synthesis 2008; 3183
• 4e D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095
• 4f Zhou J. Chem. Asian J. 2010; 5: 422
• 4g Pellissier H. Adv. Synth. Catal. 2012; 354: 237
• 5a Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134
• 5b Nicolaou KC, Chen JS. Chem. Soc. Rev. 2009; 38: 2993
• 5c Grondal C, Jeanty M, Enders D. Nature Chem. 2010; 2: 167
• 6a Das JP, Marek I. Chem. Commun. 2011; 47: 4593
• 6b Trost BM, Jiang C. Synthesis 2006; 369
• 6c Douglas CJ, Overman LE. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 5363
• 7 For a leading review, see: Overman LE, Pennington LD. J. Org. Chem. 2003; 68: 7143
• 8a Trost BM, Lee DC. J. Am. Chem. Soc. 1988; 110: 6556
• 8b Trost BM, Brandi A. J. Am. Chem. Soc. 1984; 106: 5041
• 8c Sworin M, Neumann WL. J. Org. Chem. 1988; 53: 4894
• 8d Nakamura T, Matsui T, Tanino K, Kuwajima I. J. Org. Chem. 1997; 62: 3032
• 8e Youn J.-H, Lee J, Cha JK. Org. Lett. 2001; 3: 2935
• 8f Frongia A, Girard C, Ollivier J, Piras PP, Secci F. Synlett 2008; 2823
• 8g Armstrong A, Bhonoah Y, Shanaham SE. J. Org. Chem. 2007; 72: 8019
• 8h Beaulieu M.-A, Guérard KC, Maertens G, Sabot C, Canesi S. J. Org. Chem. 2011; 76: 9460
• 8i Lavigne RM, Riou M, Girardin M, Morency L, Barriault L. Org. Lett. 2005; 7: 5921
• 9 Overman LE, Wolfe JP. J. Org. Chem. 2002; 67: 6421
• 10a Cohen F, MacMillan DW. E, Overman LE, Romero A. Org. Lett. 2001; 3: 1225
• 10b Grese TA, Hutchinson KD, Overman LE. J. Org. Chem. 1993; 58: 2468
• 11a Suhre MH, Reif M, Kirsch SF. Org. Lett. 2005; 7: 3925
• 11b Binder JT, Kirsch SF. Org. Lett. 2006; 8: 2151
• 11c Menz H, Kirsch SF. Org. Lett. 2006; 8: 4795
• 11d Harschneck T, Kirsch SF. J. Org. Chem. 2011; 76: 2145
• 11e Zhu Z.-B, Kirsch SF. Chem. Commun. 2013; 49: 2272

For reviews on π-activation catalysis, see:
• 12a Fürstner A, Davies PW. Angew. Chem. Int. Ed. 2007; 46: 3410
• 12b Hashmi AS. K. Chem. Rev. 2007; 107: 2180
• 12c Jiménez-Nuñez E, Echavarren AM. Chem. Commun. 2007; 333
• 12d Crone B, Kirsch SF. Chem. Eur. J. 2008; 14: 3514
• 12e Patil NT, Yamamoto Y. Chem. Rev. 2008; 108: 3395
• 12f Corma A, Leyva-Pérez A, Sabater MJ. Chem. Rev. 2011; 111: 1657
• 12g Duschek A, Kirsch SF. Angew. Chem. Int. Ed. 2008; 47: 5703
• 12h Shapiro ND, Toste FD. Synlett 2010; 675
• 12i Gorin DJ, Sherry BD, Toste FD. Chem. Rev. 2008; 108: 3351
• 12j Rudolph M, Hashmi AS. K. Chem. Soc. Rev. 2012; 41: 2448
• 12k Wegner HA, Auzias M. Angew. Chem. Int. Ed. 2011; 50: 3236

For reviews on electrophilic cyclizations, see:
• 13a Palisse A, Kirsch SF. Org. Biomol. Chem. 2012; 10: 8041
• 13b French AN, Bissmire S, Wirth T. Chem. Soc. Rev. 2004; 33: 354
• 13c Godoi B, Schumacher RF, Zeni G. Chem. Rev. 2011; 111: 2937

For a comparison between electrophilic and metal-catalyzed π-activation, see:
• 14a Yamamoto Y, Gridnev ID, Patil NT, Jin T. Chem. Commun. 2009; 5075
• 14b Hummel S, Kirsch SF. Beilstein J. Org. Chem. 2011; 7: 847
• 15 Kirsch SF, Binder JT, Crone B, Duschek A, Haug TT, Liébert C, Menz H. Angew. Chem. Int. Ed. 2007; 46: 2310

For examples of further works on 1,5-enyne cycloisomerizations involving π-activation, see:
• 16a Wang S, Zhang L. J. Am. Chem. Soc. 2006; 128: 14274
• 16b Marion N, de Fremont P, Lemiere G, Stevens ED, Fensterbank L, Malacria M, Nolan SP. Chem. Commun. 2006; 2048
• 16c Gagosz F. Org. Lett. 2005; 7: 4129
• 16d Zhang L, Kozmin SA. J. Am. Chem. Soc. 2004; 126: 11806
• 16e Mamane V, Gress T, Krause H, Fürstner A. J. Am. Chem. Soc. 2004; 126: 8654
• 16f Buzas AK, Istrate FM, Gagosz F. Angew. Chem. Int. Ed. 2007; 46: 1141

For reviews on the cycloisomerization of enynes, see:
• 17a Zhang L, Sun J, Kozmin SA. Adv. Synth. Catal. 2006; 348: 2271
• 17b Nieto-Oberhuber C, López S, Jiménez-Núñez E, Echavarren AM. Chem. Eur. J. 2006; 12: 5916
• 17c Michelet V, Toullec PY, Genêt JP. Angew. Chem. Int. Ed. 2008; 47: 4268
• 17d Jiménez-Nuñez E, Echavarren AM. Chem. Rev. 2008; 108: 3326
• 18 For a leading theoretical study, see: Fan T, Chen X, Sun J, Lin Z. Organometallics 2012; 31: 4221
• 19 Menz H, Binder JT, Crone B, Duschek A, Haug TT, Kirsch SF, Klahn P, Liébert C. Tetrahedron 2009; 65: 1880
• 20 For a recent study on the effect of silver salts in gold catalysis, see: Wang D, Cai R, Sharma S, Jirak J, Thummanapelli SK, Akhmedov NG, Zhang H, Liu X, Petersen JL, Shi X. J. Am. Chem. Soc. 2012; 134: 9012
• 21 Klahn P, Duschek A, Lièbert C, Kirsch SF. Org. Lett. 2012; 14: 1250
• 22a Hikino H, Aota K, Maebayashi Y, Takemoto T. Chem. Pharm. Bull. 1966; 14: 1439
• 22b Hikino H, Aota K, Maebayashi Y, Takemoto T. Chem. Pharm. Bull. 1967; 15: 1349
• 22c Kapadia VH, Naik VG, Wadia MS, Dev S. Tetrahedron Lett. 1967; 8: 4661
• 23a Krauter CM, Hashmi AS. K, Pernpointner M. ChemCatChem 2010; 2: 1226
• 23b Hashmi AS. K, Ramamurthi TD, Rominger F. Adv. Synth. Catal. 2010; 352: 971

For selected works, see:
• 24a Buzas A, Istrate F, Gagosz F. Org. Lett. 2006; 8: 1957
• 24b Ye L, Zhang L. Org. Lett. 2009; 11: 3646
• 24c Weyrauch JP, Hashmi AS. K, Schuster A, Hengst T, Schetter S, Littmann A, Rudolph M, Hamzic M, Visus J, Rominger F, Frey W, Bats JW. Chem. Eur. J. 2010; 16: 956
• 24d Liao H.-H, Liu R.-S. Chem. Commun. 2011; 47: 1339
• 24e Kong W, Fu C, Ma S. Eur. J. Org. Chem. 2010; 6545

For selected works, see:
• 25a Arimitsu S, Jacobsen JM, Hammond GB. J. Org. Chem. 2008; 73: 2886
• 25b Crone B, Kirsch SF, Umland K.-D. Angew. Chem. Int. Ed. 2010; 49: 4661
• 25c Pradal A, Nasr A, Toullec PY, Michelet V. Org. Lett. 2010; 12: 5222
• 25d Sanz R, Martínez A, García-García P, Fernàndez-Rodríguez MA, Rashid MA, Rodríguez F. Chem. Commun 2010; 46: 7427
• 25e Lim C, Rao S, Shin S. Synlett 2010; 368
• 25f Kummerlöwe G, Crone B, Kretschmer M, Kirsch SF, Luy B. Angew. Chem. Int. Ed. 2011; 50: 2643
• 25g Harschneck T, Kirsch SF, Wegener M. Synlett 2011; 1151
• 25h Yang F, Ji K.-G, Zhu H.-T, Shaukat A, Liu X.-Y, Liang Y.-M. Chem. Eur. J. 2011; 17: 4986
• 26 Huber F, Kirsch SF. J. Org. Chem. 2013; 78: 2780
• 27 Li J, Liu X, Lee D. Org. Lett. 2012; 14: 410
• 28 Hashmi AS. K, Yang W, Rominger F. Angew. Chem. Int. Ed. 2011; 50: 5762
• 29 Hashmi AS. K, Yang W, Rominger F. Chem. Eur. J. 2012; 18: 6576
• 30 For related aromatizations, see: Bhunia S, Sohel SM. A, Yang C.-C, Lush S.-F, Shen F.-M, Liu R.-S. J. Organomet. Chem. 2009; 694: 566
• 31 Korotchenko VN, Gagné MR. J. Org. Chem. 2007; 72: 4877
• 32 Huang X, Zhang L. J. Am. Chem. Soc. 2007; 129: 6398
• 33 Haug TT, Harschneck T, Duschek A, Lee C.-U, Binder JT, Menz H, Kirsch SF. J. Organomet. Chem. 2009; 694: 510
• 34 Debeleds O, Gayon E, Vrancken E, Campagne J.-M. Beilstein J. Org. Chem. 2011; 7: 866
• 35a Bae HJ, Baskar B, An SE, Cheong JY, Thangadurai DT, Hwang I.-C, Rhee YH. Angew. Chem. Int. Ed. 2008; 47: 2263
• 35b An SE, Jeong J, Baskar B, Lee J, Seo J, Rhee YH. Chem. Eur. J. 2009; 15: 11837
• 36 Baskar B, Bae HJ, An SE, Cheong JY, Rhee YH, Duschek A, Kirsch SF. Org. Lett. 2008; 10: 2605
• 37 Alcarazo M, Stork T, Anoop A, Thiel W, Fürstner A. Angew. Chem. Int. Ed. 2010; 49: 2542
• 38 For a review, see: Klahn P, Kirsch SF. ChemCatChem 2011; 3: 649
• 39a Canham SM, France DJ, Overman LE. J. Am. Chem. Soc. 2010; 132: 7876
• 39b Canham SM, France DJ, Overman LE. J. Org. Chem. 2013; 78: 9
• 40 Hirasawa Y, Morita H, Shiro M, Kobayashi J. Org. Lett. 2003; 5: 3991
• 41 Tang J.-M, Bhunia S, Sohel SM. A, Lin M.-Y, Liao H.-Y, Datta S, Das A, Liu R.-S. J. Am. Chem. Soc. 2007; 129: 15677
• 42 Sethofer SG, Staben ST, Hung OY, Toste FD. Org. Lett. 2008; 10: 4315
• 43 For a review, see: Garayalde D, Nevado C. Beilstein J. Org. Chem. 2011; 7: 767
• 44 Kirsch SF, Binder JT, Liébert C, Menz H. Angew. Chem. Int. Ed. 2006; 45: 5878
• 45 For a review on furan-3(2H)-ones, see: Haug TT, Kirsch SF. Targets Heterocycl. Syst. 2009; 13: 57

For selected syntheses of furan-3(2H)-ones, see:
• 46a Reiter M, Turner H, Mills-Webb R, Gouverneur V. J. Org. Chem. 2005; 70: 8478
• 46b Dolder M, Shao X, Tamm C. Helv. Chim. Acta 1990; 73: 63
• 46c Naruse Y, Esaki T, Yamamoto H. Tetrahedron 1988; 44: 4767
• 46d Smith AB. III, Guaciaro MA, Schow SR, Wovkulich PM, Toder BH, Hall TW. J. Am. Chem. Soc. 1981; 103: 219
• 46e Qi C, Jiang H, Huang L, Yuan G, Ren Y. Org. Lett. 2011; 13: 5520
• 46f Egi M, Azechi K, Saneto M, Shimizu K, Akai S. J. Org. Chem. 2010; 75: 2123
• 47a Yao T, Zhang X, Larock RC. J. Am. Chem. Soc. 2004; 126: 11164
• 47b Liu X, Pan Z, Shu X, Duan X, Liang Y. Synlett 2006; 1962
• 47c Zhang J, Schmalz H.-G. Angew. Chem. Int. Ed. 2006; 45: 6704
• 47d Zhang G, Huang X, Li G, Zhang L. J. Am. Chem. Soc. 2008; 130: 1814
• 47e Liu Y, Liu M, Guo S, Tu H, Gao H. Org. Lett. 2006; 8: 3445
• 47f Xiao Y, Zhang J. Angew. Chem. Int. Ed. 2008; 47: 1903

For studies on related domino reactions not involving pinacol-type rearrangements, see:
• 48a Li W, Li Y, Zhang J. Chem. Eur. J. 2010; 16: 6447
• 48b Li W, Li Y, Zhou G, Wu X, Zhang J. Chem. Eur. J. 2012; 18: 15113
• 49 Kirsch SF. J. Org. Chem. 2005; 70: 10210
• 50 Bunnelle EM, Smith CR, Lee SK, Singaram WS, Rhodes AJ, Sarpong R. Tetrahedron 2008; 64: 7008
• 51 Crone B, Kirsch SF. J. Org. Chem. 2007; 72: 5435
• 52 Binder JT, Crone B, Kirsch SF, Liébert C, Menz H. Eur. J. Org. Chem. 2007; 1636
• 53 Smith CR, Bunnelle EM, Rhodes AJ, Sarpong R. Org. Lett. 2007; 9: 1169

For a related cyclization, see:
• 54a Seregin IV, Gevorgyan V. J. Am. Chem. Soc. 2006; 128: 12050
• 54b Seregin IV, Schammel AW, Gevorgyan V. Org. Lett. 2007; 9: 3433
• 55 Choi J, Lee GH, Kim I. Synlett 2008; 1243
• 56a Kim I, Kim K. Org. Lett. 2010; 12: 2500
• 56b Chernyak D, Skontos C, Gevorgyan V. Org. Lett. 2010; 12: 3242
• 56c Cho H, Kim I. Tetrahedron 2012; 68: 5464
• 57a Shu X.-Z, Liu X.-Y, Ji KG, Xiao H.-Q, Liang Y.-M. Chem. Eur. J. 2008; 14: 5282
• 57b Wen S.-G, Liu W.-M, Liang Y.-M. J. Org. Chem. 2008; 73: 4342
• 58 Yang Y.-F, Shu X.-Z, Luo J.-Y, Ali S, Liang Y.-M. Chem. Eur. J. 2012; 18: 8600
• 59a Hashmi AS. K, Schwarz L, Choi J.-H, Frost TM. Angew. Chem. Int. Ed. 2000; 39: 2285
• 59b Labsch S, Ye S, Adler A, Neudörfl J.-M, Schmalz H.-G. Tetrahedron: Asymmetry 2010; 21: 1745
• 60 Umland K.-D, Palisse A, Haug TT, Kirsch SF. Angew. Chem. Int. Ed. 2011; 50: 9965
• 61a Stoltz BM, Wood JL. Tetrahedron Lett. 1996; 37: 3929
• 61b Wood JL, Stoltz BM, Goodman SN, Onwueme K. J. Am. Chem. Soc. 1997; 119: 9652
• 62 Yeom H.-S, Lee Y, Jeong J, So E, Hwang S, Lee J.-E, Sung S, Shin S. Angew. Chem. Int. Ed. 2010; 49: 1611
• 63 Leemans E, D’hooge M, De Kimpe N. Chem. Rev. 2011; 111: 3268
• 64 Liu L, Zhang J. Angew. Chem. Int. Ed. 2009; 48: 6093
• 65 Markham JP, Staben ST, Toste FD. J. Am. Chem. Soc. 2005; 127: 9708

For related Wagner–Meerwein shifts, see:
• 66a Fürstner A, Aïssa C. J. Am. Chem. Soc. 2006; 128: 6306
• 66b Yoshida M, Maeyama Y, Al-Amin M, Shishido K. J. Org. Chem. 2011; 76: 5813
• 67 Kleinbeck F, Toste FD. J. Am. Chem. Soc. 2009; 131: 9178
• 68 Yao L.-F, Wei Y, Shi M. J. Org. Chem. 2009; 74: 9466
• 69 Lange A, Heydenreuther W, Menz H, Kirsch SF. Synlett 2009; 2987
• 70 Zhu L.-L, Li X.-X, Zhou W, Li X, Chen Z. J. Org. Chem. 2011; 76: 8014
• 71 Jiménez-Núñez E, Claverie CK, Nieto-Oberhuber C, Echavarren AM. Angew. Chem. Int. Ed. 2006; 45: 5452