Sequential Addition and Cyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

Giorgio Abbiati; Antonio Arcadi; Fabio Marinelli; Elisabetta Rossi

doi:10.1055/s-0033-1338594

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(06): 687-721
DOI: 10.1055/s-0033-1338594

review

Sequential Addition and Cyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

Giorgio Abbiati

^aDipartimento di Scienze Farmaceutiche – Sezione di Chimica Generale e Organica ‘A. Marchesini’, Università degli Studi di Milano, via G. Venezian 21, 20133 Milano, Italy

,

Antonio Arcadi*

^bDipartimento di Scienze Fisiche e Chimiche, Università degli Studi dell’Aquila, Via Vetoio, 67010 Coppito, L’Aquila, Italy Fax: +39(0862)433033 eMail: antonio.arcadi@univaq.it

,

Fabio Marinelli

^bDipartimento di Scienze Fisiche e Chimiche, Università degli Studi dell’Aquila, Via Vetoio, 67010 Coppito, L’Aquila, Italy Fax: +39(0862)433033 eMail: antonio.arcadi@univaq.it

,

Elisabetta Rossi

^aDipartimento di Scienze Farmaceutiche – Sezione di Chimica Generale e Organica ‘A. Marchesini’, Università degli Studi di Milano, via G. Venezian 21, 20133 Milano, Italy

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

This review examines sequential processes involving α,β-ynones and α,β-ynoates containing proximate nucleophiles as useful building blocks for the synthesis of heterocyclic derivatives through conjugate-addition-type, pericyclic and transition-metal-catalyzed transfer hydrogenation, hydroarylation, hydrovinylation, or hydroalkynylation reactions followed by heterocyclization.

1 Introduction

2 Conjugate Addition–Heterocyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

2.1 Conjugate Addition–Annulation Reactions of β-(2-Aminoaryl or Heteroaryl)-α,β-Ynones

2.2 Sequential Reactions of γ-Hydroxy-α,β-Acetylenic Esters with Nucleophilic Reagents

2.3 Sequential Electrophilic Addition–Annulation Processes of α,β-Ynones Containing Proximate Nucleophiles

3 Cycloaddition–Heterocyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

3.1 [2+2] and [4+2] Cycloaddition–Annulation Reactions

3.2 1,3-Dipolar Cycloaddition–Annulation Reactions

4 Transition-Metal-Catalyzed Addition–Heterocyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

4.1 Palladium-Catalyzed Transfer Hydrogenation–Heterocyclization Processes

4.2 Palladium-Catalyzed Hydroarylation–Heterocyclization Processes

4.3 Rhodium-Catalyzed Hydroarylation–Heterocyclization Processes

4.4 Copper-Catalyzed Hydroarylation–Heterocyclization Processes

4.5 Transition-Metal-Catalyzed Hydrovinylation–Heterocyclization Processes

4.6 Transition-Metal-Catalyzed Hydroalkynylation–Heterocyclization Processes

5 Conclusion

Key words

aminoalkynones - hydroxyalkynoates - sequential reactions - annulation - heterocycles

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Referenzen

References

1a Gouault N, Le Roch M, Cheignon A, Uriac P, David M. Org. Lett. 2011; 13: 4371
1b Xu B.-H, Kehr G, Fröhlic R, Wibbeling B, Schirmer B, Grimme S, Erker G. Angew. Chem. Int. Ed. 2011; 50: 7183
1c Trost BM, Taft BR, Masters JT, Lumb J.-P. J. Am. Chem. Soc. 2011; 133: 8502

2a Niphakis MJ, Turunen BJ, Georg GI. J. Org. Chem. 2010; 75: 6793
2b Acharya HP, Clive DL. J. J. Org. Chem. 2010; 75: 5223
2c Gouault N, Le Roch M, Cornée C, David M, Uriac P. J. Org. Chem. 2009; 74: 5614
2d Turunen BJ, Georg GI. J. Am. Chem. Soc. 2006; 128: 8702
2e Ishikawa T, Aikawa T, Watanabe S, Saito S. Org. Lett. 2006; 8: 3881
2f Muthiah C, Arai MA, Shinohara T, Arai T, Takizawa S, Sasai H. Tetrahedron Lett. 2003; 44: 5201

3a Kakinuma T, Oriyama T. Tetrahedron Lett. 2010; 51: 290
3b Cacchi S, Fabrizi G, Filisti E. Org. Lett. 2008; 10: 2629
3c Zhou Q.-F, Yang F, Guo Q.-X, Xue S. Synlett 2007; 215
3d Gridley JJ, Coogan MP, Knight DW, Abdul Malik KM, Sharland CM, Singkhonrat J, Williams S. Chem. Commun. 2003; 2550
3e Sneddon HF, Gaunt MJ, Ley V. Org. Lett. 2003; 5: 1147

4a Wang H, Denton JR, Davies HM. L. Org. Lett. 2011; 13: 4316
4b Wang L, Li G, Liu Y. Org. Lett. 2011; 13: 3786
4c Körber N, Rominger F, Müller TJ. J. Synlett 2010; 782
4d Mueller AJ, Jennings MP, Dieter R. Org. Lett. 2007; 9: 5327
4e Dieter RK, Lu K. J. Org. Chem. 2002; 67: 847
4f Hanzawa Y, Tabuchi N, Narita K, Kakuuchi A, Yabe M, Taguchi T. Tetrahedron 2002; 58: 7559
4g Nilsson K, Andersson T, Ullenius C. J. Organomet. Chem. 1997; 545-546: 591

5a Girardin M, Dolman SJ, Lauzon S, Ouellet SG, Hughes G, Fernandez P, Zhou G, O’Shea PD. Org. Process Res. Dev. 2011; 15: 1073
5b Shi F, Luo SW, Tao Z.-L, He L, Yu J, Tu S.-J, Gong L.-Z. Org. Lett. 2011; 13: 4680
5c Johnston KA, Allcock RW, Jiang Z, Collier ID, Blakli H, Rosair GM, Bailey PD, Morgan KM, Kohno Y, Adams DR. Org. Biomol. Chem. 2008; 6: 175

6a Merkul E, Dohe J, Gers C, Rominger F, Müller TJ. J. Angew. Chem. Int. Ed. 2011; 50: 2966
6b Bannwarth P, Grée D, Grée R. Tetrahedron Lett. 2010; 51: 2413
6c Zohreh N, Alizadeh A. Tetrahedron 2011; 67: 4595
6d Bannwarth P, Valleix A, Grée D, Grée R. J. Org. Chem. 2009; 74: 4646
6e Dastrup DM, Yap AH, Weinreb SM, Henryb JR, Lechleiter AJ. Tetrahedron 2004; 60: 901

7a Zora M, Kivrak A, Yazici C. J. Org. Chem. 2011; 76: 6726
7b Ueda M, Ikeda Y, Sato A, Ito Y, Kakiuchi M, Shono H, Miyoshi T, Naito T, Miyata O. Tetrahedron 2011; 67: 4612
7c Praveen C, Kalyanasundaram A, Perumal PT. Synlett 2010; 777
7d Ueda M, Sato A, Ikeda Y, Miyoshi T, Naito T, Miyata O. Org. Lett. 2010; 12: 2594
7e Waldo JP, Larock RC. J. Org. Chem. 2007; 72: 9643
7f Waldo JP, Larock RC. Org. Lett. 2005; 7: 5203
7g Bishop BB, Brands KM. J, Gibb AD, Kennedy DJ. Synthesis 2004; 43
7h Grotjahn DB, Van S, Combs D, Lev DA, Schneider C, Rideout M, Meyer C, Hernandez G, Mejorado L. J. Org. Chem. 2002; 67: 9200

8a Gers CF, Rosellen J, Merkul E, Müller TJ. J. Beilstein J. Org. Chem. 2011; 7: 1173
8b Muschelknautz C, Frank W, Müller TJ. J. Org. Lett. 2011; 13: 2556
8c Willy B, Müller TJ. J. Org. Lett. 2011; 13: 2082
8d Grotkopp O, Ahmad A, Frank W, Müller TJ. J. Org. Biomol. Chem. 2011; 9: 8130
8e Rotzoll S, Willy B, Schönhaber J, Rominger F, Müller TJ. J. Eur. J. Org. Chem. 2010; 3516
8f Willy B, Frank W, Müller TJ. J. Org. Biomol. Chem. 2010; 8: 90
8g Willy B, Müller TJ. J. Curr. Org. Chem. 2009; 13: 1777
8h Merkul E, Grotkopp O, Müller TJ. J. Synthesis 2009; 502
8i Liu H.-L, Jiang H.-F, Zhang M, Yao W.-J, Zhu Q.-H, Tang Z. Tetrahedron Lett. 2008; 49: 3805
8j Willy B, Müller TJ. J. ARKIVOC 2008; (i): 195
8k Merkul E, Müller TJ. J. Chem. Commun. 2006; 4817
8l Ahmed MS. M, Kobayashi K, Mori A. Org. Lett. 2005; 7: 4487

9a Kurhade SE, Salunkhe VT, Siddaiah V, Bhuniya D, Masquelin T, Reddy DS. Synthesis 2011; 3523
9b Fuchs FC, Eller GA. Molecules 2009; 14: 3814
9c Shvartsberg MS, Ivanchikova ID. ARKIVOC 2003; (xiii): 87
9d Obrecht D. Tetrahedron 1997; 53: 641

10 Arcadi A, Cacchi S, Marinelli F, Pace P, Sanzi G. Synlett 1995; 823

11a Dell’Acqua MG, Abbiati G, Arcadi A, Rossi E. Org. Biomol. Chem. 2011; 9: 7836
11b Arcadi A, Abbiati G, Rossi E. J. Organomet. Chem. 2011; 696: 87
11c Alfonsi M, Dell’Acqua M, Facoetti D, Arcadi A, Abbiati G, Rossi E. Eur. J. Org. Chem. 2009; 2852
11d Abbiati G, Arcadi A, Bellinazzi A, Beccalli E, Rossi E, Zanzola S. J. Org. Chem. 2005; 70: 4088
11e Arcadi A, Cacchi S, Fabrizi G, Marinelli F, Parisi LM. Tetrahedron 2003; 59: 4661
11f Abbiati G, Arcadi A, Beccalli E, Rossi E. Tetrahedron Lett. 2003; 44: 5331
11g Arcadi A, Di Giuseppe S, Marinelli F, Rossi E. Tetrahedron: Asymmetry 2001; 12: 2715
11h Arcadi A, Di Giuseppe S, Marinelli F, Rossi E. Adv. Synth. Catal. 2001; 343: 443
11i Arcadi A, Attanasi OA, Guidi B, Rossi E, Santeusanio S. Eur. J. Org. Chem. 1999; 3117
11j Arcadi A, Attanasi OA, Guidi B, Rossi E, Santeusanio S. Chem. Lett. 1999; 59
11k Arcadi A, Rossi E. Tetrahedron 1998; 54: 15253
11l Arcadi A, Anacardio R, D’Anniballe G, Gentile M. Synlett 1997; 1315
11m Arcadi A, Rossi E. Synlett 1997; 667
11n Arcadi A, Marinelli F, Pini E, Rossi E. Tetrahedron Lett. 1996; 37: 3387
11o Arcadi A, Rossi E. Tetrahedron Lett. 1996; 37: 6811
11p Arcadi A, Cacchi S, Larock RC, Marinelli F. Tetrahedron Lett. 1993; 34: 2813
11q Arcadi A, Cacchi S, Marinelli F, Pace P. Synlett 1993; 741
11r Arcadi A, Cacchi S, Fabrizi G, Marinelli F. Synlett 1993; 65

12 Wu X.-F, Neumann H, Beller M. Chem. Eur. J. 2010; 16: 12104; and references therein
13 Cacchi S, Fabrizi G, Marinelli F. Synlett 1999; 401
14 Arcadi A, Marinelli F, Rossi E. Tetrahedron 1999; 55: 13233
15 Arcadi A, Chiarini M, Marinelli F, Picchini S. Synthesis 2011; 4084
16 Abbiati G, Arcadi A, Marinelli F, Rossi E. Synthesis 2002; 1912
17 Yakovleva EA, Ivanchikova ID, Shvartsberg MS. Russ. Chem. Bull., Int. Ed. 2005; 54: 421
18 Rossi E, Abbiati G, Canevari V, Nava D, Arcadi A. Tetrahedron 2004; 60: 11391
19 Torii S, Xu LH, Sadakane M, Okumoto H. Synlett 1992; 513
20 Abbiati G, Arcadi A, Canevari V, Capezzuto L, Rossi E. J. Org. Chem. 2005; 70: 6454

21a Pohlki F, Doye S. Chem. Soc. Rev. 2003; 32: 104
21b Shimada T, Yamamoto Y. J. Am. Chem. Soc. 2002; 124: 12670
21c Müller TE, Beller M. Chem. Rev. 1998; 98: 675

22 Kobayashi S, Kakumoto K, Sugiura M. Org. Lett. 2002; 4: 13192
23 Mizushima E, Hayashi T, Tanaka M. Org. Lett. 2003; 5: 3349
24 Asao N, Nogami T, Takanashi K, Yamamoto Y. J. Am. Chem. Soc. 2002; 124: 764
25 Arcadi A, Bianchi G, Inesi A, Marinelli F, Rossi L. Synlett 2007; 1031

26a Lund H In Organic Electrochemistry. 4th ed.; Lund H, Hammerich O. Marcel Dekker; New York: 2001
26b Bard AJ, Stratmann M. Encyclopedia of Electrochemistry, Organic Electrochemistry. Vol. 8. Schäfer HJ. Wiley-VCH; Weinheim: 2004
26c Torii S. Electroorganic Reduction Synthesis. Vols. 1 and 2. Wiley-VCH; Weinheim: 2006

27a Pace V, Castoldi A, Alcára AR, Holze W. Green Chem. 2012; 14: 1859
27b Gao G, Pu L. Sci. China Chem. 2010; 53: 21
27c Tejedor D, López-Tosco S, Cruz-Acosta F, Méndez-Abt G, García-Tellado F. Angew. Chem. Int. Ed. 2009; 48: 2090
27d Trost BM, Weiss AH. Adv. Synth. Catal. 2009; 351: 963
27e Shahi SP, Koide K. Angew. Chem. Int. Ed. 2004; 43: 2525
27f Ishikawa T, Mizuta T, Hagiwara K, Aikawa T, Kudo T, Saito S. J. Org. Chem. 2003; 68: 3702
27g Midland MM, Tramontano A, Cable JR. J. Org. Chem. 1980; 45: 28

28 Jones ER. H, Whiting MC. J. Chem. Soc. 1949; 1423

29a Gunasckera SP, McCarthy PJ, Kelly-Borges M, Lolkousky E, Clardy J. J. Am. Chem. Soc. 1996; 118: 8759
29b Schmidt EW, Faulkner DJ. Tetrahedron Lett. 1996; 37: 3951
29c He H, Kulanthaivel P, Baker BJ. Tetrahedron Lett. 1994; 35: 7189
29d Potts BC. M, Faulkner DJ, de Carvalho MS, Jacobs RS. J. Am. Chem. Soc. 1992; 114: 5093
29e de Silva ED, Scheuer PJ. Tetrahedron Lett. 1980; 21: 1611

Selected examples:

30a Dai S.-J, Tao J.-Y, Liu K, Jiang Y.-T, Shen L. Phytochemistry 2006; 67: 1326
30b Bousserouel H, Litaudon M, Morleo B, Martin M.-T, Thoison O, Nosjean O, Boutin JA, Renard P, Sévenet T. Tetrahedron 2005; 61: 845
30c Van Quaquebeke E, Simon G, André A, Dewelle J, El Yazidi M, Bruyneel F, Tuti J, Nacoulma O, Guissou P, Decaestecker C, Braekman J.-C, Kiss R, Darro F. J. Med. Chem. 2005; 48: 849
30d Lattmann E, Dunn S, Niamsanit S, Sattayasai N. Bioorg. Med. Chem. Lett. 2005; 15: 919

31 Ortega MJ, Zubía E, Ocaña GM, Naranjo S, Salvá J. Tetrahedron 2000; 56: 3963

32a Mavrov MV, Konyushkin LD, Simirskaya NI, Zlotin SG. Russ. Chem. Bull., Int. Ed. 2005; 54: 2857
32b Mavrov MV, Simirskaya NI. Chem. Heterocycl. Compd. 1999; 10: 1150

33 Zhou L.-H, Yu X.-Q, Pu L. J. Org. Chem. 2009; 74: 2013
34 Gabriele B, Salerno G, Plastina P, Costa M, Crispini A. Adv. Synth. Catal. 2004; 346: 351
35 Tejedor D, Santos-Expósito A, García-Tellado F. Synlett 2006; 10: 1607; and references therein
36 Simirskaya NI, Ignat’ev NV, Schulte M, Zlotin SG. Mendeleev Commun. 2011; 21: 94
37 Arcadi A, Alfonsi M, Marinelli F. Tetrahedron Lett. 2009; 50: 2060
38 Witiak DT, Tehim AS. J. Org. Chem. 1987; 52: 2324

39a Taniguchi T, Tanabe G, Muraoka O, Ishibashi H. Org. Lett. 2008; 10: 197
39b Taniguchi T, Ishibashi H. Tetrahedron 2008; 64: 8773

40 Clemo NG, Pattenden G. J. Chem. Soc., Perkin Trans. 1 1985; 2407
41 Zoss AO, Hennion GF. J. Am. Chem. Soc. 1941; 63: 1151
42 Raphael RA. J. Chem. Soc. 1947; 805
43 Saimoto H, Shinoda M, Matsubara S, Oshima K. Bull. Chem. Soc. Jpn. 1983; 56: 3088
44 Teles JH, Brode S, Chabanas M. Angew. Chem. Int. Ed. 1998; 37: 1415
45 Ramón R, Pottier C, Gómez-Suárez A, Nolan SP. Adv. Synt. Catal. 2011; 353: 1575
46 Hashmi AS. K. Angew. Chem. Int. Ed. 2010; 31: 5232
47 Rajaram AR, Pu L. Org. Lett. 2006; 10: 2019

48a Sniady A, Wheeler KA, Dembinski R. Org. Lett. 2005; 7: 1769
48b Yao T, Zhang X, Larock RC. J. Org. Chem. 2005; 70: 7679
48c Bew SP, El-Taeb GM. M, Jones S, Knight DW, Tan W.-F. Eur. J. Org. Chem. 2007; 5759
48d Huang X, Fu W, Miao M. Tetrahedron Lett. 2008; 49: 2359

49 Obrecht D. Helv. Chim. Acta 1989; 72: 447
50 Merkul E, Boersch C, Frank W, Müller TJ. J. Org. Lett. 2009; 11: 2269

51a Yang F, Jin T, Bao M, Yamamoto Y. Chem. Commun. 2011; 4541
51b Yang F, Jin T, Bao M, Yamamoto Y. Tetrahedron 2011; 67: 10147

52 Karpov AS, Merkul E, Oeser T, Müller TJ. J. Eur. J. Org Chem. 2006; 2991

53a Cook AG In Enamines: Synthesis, Structure, and Reactions. 2nd ed.; Cook AG. Marcel Dekker; New York: 1988: Chap. 7, 384-388
53b Tunoglu N, Uludag N. Org. Prep. Proced. Int. 1997; 29: 541
53c Hongo H, Nakano H, Okuyama Y. Heterocycles 1995; 40: 831
53d Kaupp G, Pogodda U, Atfah A, Meier H, Vierengel A. Angew. Chem. Int. Ed. 1992; 31: 768

54 Rossi E, Abbiati G, Arcadi A, Marinelli F. Tetrahedron Lett. 2001; 42: 3705

55a Tsuge O, Hatta T, Takahashi Y, Maeda H, Kakahi A. Heterocycles 1998; 47: 665
55b Bengtson G, Keyaniyan S, De Meijere A. Chem. Ber. 1986; 119: 3607
55c Kuroda S, Hirooka S, Iwaki H, Ikeda M, Takeshi N, Ogisu M, Yasunami M, Takase K. Chem. Lett. 1986; 2039
55d Van Beek G, Van der Baan JL, Klumpp GW, Bickelhaupt F. Tetrahedron 1986; 42: 5111

56 Cook AG In Enamines: Synthesis, Structure, and Reaction. 2nd ed.; Cook AG. Marcel Dekker; New York: 1988: Chap. 1, 1-27
57 Wills MS. B, Danheiser RL. J. Am. Chem. Soc. 1998; 120: 9378
58 Anker RM, Cook AH. J. Chem. Soc. 1948; 806
59 Overberger CG, Kabasakalian P. J. Am. Chem. Soc. 1957; 79: 3182
60 Madapa S, Sridhar D, Yadav GP, Maulik PR, Batra S. Eur. J. Org. Chem. 2007; 4343
61 Bonjouklian R, York JS. PCT Int. Appl. WO2002000624, 2002
62 Humbert D, Gasc J.-C, Hunt PF. Patent US4588731, 1986
63 Abbiati G, Arcadi A, Marinelli F, Rossi E. Eur. J. Org. Chem. 2003; 1423

64a Gasco A, Bulton AJ In Advances in Heterocyclic Chemistry. Vol. 29. Katritzky AR. Academic Press; Orlando: 1981
64b Sliwa W, Thomas A. Heterocycles 1985; 23: 399

65 Grünanger P, Vita-Finzi P In The Chemistry of Heterocyclic Compounds. Vol. 49. Weissberger A, Taylor EC. John Wiley; New York: 1999
66 Merino P In Science of Synthesis. Vol. 27. Padwa A. Thieme; Stuttgart: 2004: 511-580
67 Grigor’ev IA In Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis. Feuer H. Wiley-VCH; Weinheim: 2008. Chap. 2
68 Martin J, Jones JR. C. F In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and NaturalProducts. Padwa A, Pearson WH. Wiley-VCH; Weinheim: 2002. Chap. 1
69 Ruck-Braun K, Freysoldt TH. E, Wierschem F. Chem. Soc. Rev. 2005; 34: 507
70 Tufariello JJ In 1,3-Dipolar Cycloaddition Chemistry. Vol. 2. Padwa A. John Wiley & Sons; New York: 1984: 83-167
71 Grunanger P, Vita-Finzi P In The Chemistry of Heterocyclic Compounds. Taylor EC. John Wiley & Sons; New York: 1991. Part 1, 630-637
72 Abbiati G, Arcadi A, Marinelli F, Rossi E, Verdecchia M. Eur. J. Org. Chem. 2009; 1027
73 Ager DJ In Handbook for Homogeneous Hydrogenation. Vol. 2. de Vries JG, Elsevier CJ. Wiley-VCH; Weinheim: 2007: 745-772

74a Sajiki H, Mori S, Ohkubo T, Ikawa T, Kume A, Maegawa T, Monguchi Y. Chem. Eur. J. 2008; 14: 5109
74b Nishimura S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis. Wiley; New York: 2001
74c Siegel S In Comprehensive Organic Chemistry. Vol. 8. Trost BM, Fleming I, Semmelhack MF. Pergamon Press; Oxford: 1991. Chap. 3.1

75a Ito M, Koo L.-W, Himizu A, Kobayashi C, Sakaguchi A, Ikariya T. Angew. Chem. Int. Ed. 2009; 48: 1324
75b Takaya H, Noyori R In Comprehensive Organic Chemistry. Vol. 8. Trost BM, Fleming I, Semmelhack MF. Pergamon Press; Oxford: 1991. Chap. 3.2

76a Weir JR, Patel BA, Heck RF. J. Org. Chem. 1980; 45: 4926
76b Cortese NA, Heck R. J. Org. Chem. 1978; 43: 3985

77 Arcadi A, Bernocchi E, Burini A, Cacchi S, Marinelli F, Pietroni B. Tetrahedron 1988; 44: 481
78 Arcadi A, Bernocchi E, Cacchi S, Marinelli F. Synlett 1991; 27
79 Arcadi A, Cacchi S, Marinelli F, Misiti D. Tetrahedron Lett. 1998; 29: 1457

80a Arcadi A, Cacchi S, Marinelli F, Adovisio V, Nardelli N. Gazz. Chim. Ital. 1992; 122: 127
80b Arcadi A, Bernocchi E, Cacchi S, Marinelli F, Scarinci A. Synlett 1991; 177

81a Meta CT, Koide K. Org. Lett. 2004; 6: 1785
81b Arcadi A, Cacchi S, Carelli I, Curulli A, Inesi A, Marinelli F. Synlett 1990; 408

82a Arcadi A, Cacchi S, Marinelli F. Tetrahedron Lett. 1986; 27: 6397
82b Arcadi A, Cacchi S, Marinelli F. Tetrahedron 1985; 41: 5121
82c Cacchi S, Felici M, Pietroni B. Tetrahedron Lett. 1984; 25: 3137

83a Oh CH, Jung HH, Kim KS. Angew. Chem. Int. Ed. 2003; 42: 805
83b Oh CH, Jung HH, Sung HR, Kim JD. Tetrahedron 2001; 57: 1723

84a Oh CH, Kim KS, Gupta AK. Chem. Commun. 2004; 22: 618
84b Itami K, Kamei T, Yoshida J.-I. J. Am. Chem. Soc. 2003; 125: 14670

85 Oh CH, Sung HR. Bull. Korean Chem. Soc. 2003; 24: 1563
86 Oh CH, Park SJ, Ryu JH, Gupta AK. Tetrahedron Lett. 2004; 45: 7039
87 Arcadi S, Aschi M, Marinelli F, Verdecchia M. Tetrahedron 2008; 64: 5354
88 Amatore C, Jutand A, Thuilliez A. Organometallics 2001; 20: 3241
89 Yamamoto Y, Suzuky R, Hattori K, Nishiyama H. Synlett 2006; 1027
90 Monteiro N, Balme G, Gore J. Tetrahedron Lett. 1991; 32: 1645
91 Quian R, Guo H, Liao Y, Guo Y, Ma S. Angew. Chem. Int. Ed. 2005; 44: 4771
92 Dieck HA, Heck RF. J. Org. Chem. 1975; 40: 1083
93 Cacchi S, Fabrizi G, Marinelli F, Moro L, Pace P. Tetrahedron 1996; 52: 10225
94 Ahlquist M, Fabrizi G, Cacchi S, Norrby PO. J. Am. Chem. Soc. 2006; 128: 12785
95 Adamo C, Amatore C, Ciofini I, Jutand A, Lakmini H. J. Am. Chem. Soc. 2006; 128: 6829

96a Genin E, Michelet V, Genêt JP. J. Organomet. Chem. 2004; 689: 3820
96b Genin E, Michelet V, Genêt JP. Tetrahedron Lett. 2004; 45: 4157
96c Lautens M, Yoshida M. J. Org. Chem. 2003; 68: 762
96d Lautens M, Yoshida M. Org. Lett. 2002; 4: 123
96e Hayashi T, Inoue K, Taniguchi N, Ogasawara M. J. Am. Chem. Soc. 2001; 123: 9918

97 Abbiati G, Arcadi A, Marinelli F, Rossi E, Verdecchia M. Synlett 2006; 3218
98 Alfonsi M, Arcadi A, Chiarini M, Marinelli F. J. Org. Chem. 2007; 72: 9510
99 Dhondi PK, Chisholm JD. Org. Lett. 2006; 8: 67

100a Bruss AJ, Gelesky MA, Machado G, Dupont J. J. Mol. Catal. A: Chem. 2006; 252: 212
100b Bronger RP. J, Bermon JP, Herwig J, Kamer PC. J, van Leeuwen PW. N. M. Adv. Synth. Catal. 2004; 346: 789

101 Miura T, Takahashi Y, Muratami M. Chem. Commun. 2007; 595
102 Arao T, Kondo K, Aoyama T. Tetrahedron Lett. 2007; 48: 4115
103 Molander GA, Ellis N. Acc. Chem. Res. 2007; 40: 275
104 Nambo M, Noyori R, Itami K. J. Am. Chem. Soc. 2007; 129: 8080
105 Yamamoto Y, Kirai N, Harada Y. Chem. Commun. 2008; 2010
106 Nishikawa TY, Yamamoto Y, Miyaura N. Organometallics 2004; 23: 4317
107 Ahlquist M, Nielsen TE, Le Quement S, Tanner D, Norrby PO. Chem. Eur. J. 2006; 12: 2866
108 Lee J.-E, Kwon J, Yun J. Chem. Commun. 2008; 733
109 Yamamoto Y, Kirai N. Org. Lett. 2008; 24: 5513
110 Yamamoto Y, Kirai N. Heterocycles 2010; 80: 269
111 Arcadi A, Bernocchi E, Burini A, Cacchi S, Marinelli F, Pietroni B. Tetrahedron Lett. 1989; 30: 3465
112 Arcadi A, Cacchi S, Fabrizi G, Marinelli F, Pace P. Eur. J. Org. Chem. 1999; 3305
113 Trost BM, McIntosh MC. J. Am. Chem. Soc. 1995; 117: 7255
114 Trost BM, Frontier AJ. J. Am. Chem. Soc. 2000; 122: 11727
115 Trost BM, Lumb J.-L, Azzarelli MJ. J. Am. Chem. Soc. 2011; 133: 740