Palladium-Catalyzed Synthesis of Carbo- and Heterocycles through Norbornene-Mediated ortho C–H Functionalization

Raffaella Ferraccioli

doi:10.1055/s-0032-1318218

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(5): 581-591
DOI: 10.1055/s-0032-1318218

short review

Palladium-Catalyzed Synthesis of Carbo- and Heterocycles through Norbornene-Mediated ortho C–H Functionalization

Raffaella Ferraccioli*

CNR-Istituto di Scienze e Tecnologie Molecolari (ISTM), Via C. Golgi 19, 20133 Milano, Italy Fax: +39(2)50314139 eMail: Raffaella.Ferraccioli@istm.cnr.it

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Abstract

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Abstract

Direct aromatic functionalization based on the use of a palladium catalyst and norbornene is a useful method to achieve straightforward synthesis of carbo- and heterocyclic compounds. New ring formation occurs through a cascade process triggered by ortho C–H alkylation (inter- and intramolecular) or arylation (homo- and heterocoupling) of aryl iodides. Up to four new carbon–carbon bonds are generated under palladium control in a single operation.

1 Introduction

2 ortho C–H Alkylation

2.1 Intermolecular ortho C–H Alkylation

2.1.1 Heck Reaction

2.1.2 C–N Coupling

2.1.3 C–H Arylation

2.2 Intramolecular ortho C–H Alkylation

2.2.1 Heck Reaction

2.2.2 Cyanation Coupling

2.3 Coupling Inter- and Intramolecular ortho C–H Alkylation

3 ortho C–H Arylation

3.1 Homocoupling

3.2 Heterocoupling

3.2.1 α-Arylation/CO Addition

3.2.2 Heck Reaction

3.2.3 C–N Coupling

4 Conclusion

Key words

palladacycle - norbornene - C–H arylation - C–H alkylation - polycycles

Volltext

Referenzen

References

1a Facomprè M, Tardy C, Bal-Mahieu C, Colson P, Perez C, Manzanares I, Cuevas C, Bailly C. Cancer Res. 2003; 63: 7392
1b Feringa BL. J. Org. Chem. 2007; 72: 6635
1c Monte AP, Waldman SR, Marona-Lewicka D, Wainscott DB, Nelson DL, Sanders-Bush E, Nichols DE. J. Med. Chem. 1997; 40: 2997
1d Zhang Q, Tu G, Zhao Y, Cheng T. Tetrahedron 2002; 58: 6795
1e Ting PC, Lee JF, Albanese MM, Tom WC, Solomon DM, Aslanian R, Shih N.-Y, West R. Bioorg. Med. Chem. Lett. 2002; 12: 2643
1f Kimura M, Kuwano S, Sawaki Y, Fujikawa H, Noda K, Taga Y, Takagi K. J. Mater. Chem. 2005; 15: 2393
1g Makhey D, Gatto B, Yu C, Liu A, Liu LF, LaVoie EJ. Bioorg. Med. Chem. 1996; 4: 781

For selected reviews on carbo- and heterocycle synthesis through Pd-catalyzed cross-coupling reactions, see:

2a Cacchi S, Fabrizi G. Chem. Rev. 2005; 105: 2873
2b Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
2c Zeni G, Larock RC. Chem. Rev. 2006; 106: 4644

3 Trost BM. Science (Washington D.C.) 1991; 254: 1471

For recent reviews on Pd-catalyzed C–H/C–C or C–heteroatom functionalization, see:

4a Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
4b McGlacken GP, Bateman LM. Chem. Soc. Rev. 2009; 38: 2447
4c Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
4d Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
4e Chiusoli GP, Catellani M, Costa M, Motti E, Della Cá N, Maestri G. Coord. Chem. Rev. 2010; 254: 456
4f Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
4g Livendahl M, Echavarren MA. Isr. J. Chem. 2010; 50: 630
4h Ackermann L. Chem. Rev. 2011; 111: 1315

5 Tremont SJ, Rahman HU. J. Am. Chem. Soc. 1984; 106: 5759
6 Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074

7a Shabashov D, Daugulis O. J. Org. Chem. 2007; 72: 7720
7b Zhang Y.-H, Shi B.-F, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 6097

For reviews on heterocycle synthesis through direct functionalization, see:

8a Zhang M. Adv. Synth. Catal. 2009; 351: 2243
8b Thansandote P, Lautens M. Chem. Eur. J. 2009; 15: 5874
8c Mei T.-S, Kou L, Sandy M, Engle KM, Yu J.-Q. Synthesis 2012; 44: 1778
8d Ferraccioli R. Curr. Org. Synth. 2012; 9: 96

For recent examples about the use of removable directing groups, see:

9a Campeau L.-C, Rousseaux S, Fagnou K. J. Am. Chem. Soc. 2005; 127: 18020
9b Leclerc J.-P, Fagnou K. Angew. Chem. Int. Ed. 2006; 45: 7781
9c Larivèe A, Mousseau JJ, Charette AB. J. Am. Chem. Soc. 2008; 130: 52
9d Mousseau JJ, Larivèe A, Charette AB. Org. Lett. 2008; 10: 1641
9e Mousseau JJ, Bull JA, Charette AB. Angew. Chem. Int. Ed. 2010; 49: 1115

Palladium and norbornene catalyzed o-C–H alkylation/vinylation:

10a Catellani M, Frignani F, Rangoni A. Angew. Chem., Int. Ed. Engl. 1997; 36: 119
10b Catellani M, Cugini F. Tetrahedron 1999; 55: 6595
10c Cárdenas DJ, Martín-Matute B, Echavarren AM. J. Am. Chem. Soc. 2006; 128: 5034

Pd/norbornene-catalyzed o-C–H arylation/vinylation:

11a Motti E, Ippomei G, Deledda S, Catellani M. Synthesis 2003; 2671
11b Faccini F, Motti E, Catellani M. J. Am. Chem. Soc. 2004; 126: 78

For mechanistic studies of C–H cleavage by Pd(II), see:

12a Ryabov AD, Sakodinskaya IK, Yatsimirsky AK. J. Chem. Soc., Dalton Trans. 1985; 2629
12b Canty AJ, van Koten G. Acc. Chem. Res. 1995; 28: 406
12c Gómez M, Granell J, Martinez M. J. Chem. Soc., Dalton Trans. 1998; 37
12d Davies DL, Donald SM. A, Macgregor SA. J. Am. Chem. Soc. 2005; 127: 13754
12e For a recent review, see: Lapointe D, Fagnou K. Chem. Lett. 2010; 39: 1118

For reviews on palladacycles, see:

13a Dyker G. Chem. Ber. 1997; 130: 1567
13b Dupont J, Consorti CS, Spencer J. Chem. Rev. 2005; 105: 2527

For recent reviews on palladium(IV) chemistry, see:

14a Xu L.-M, Li B.-J, Yang Z, Shi Z.-J. Chem. Soc. Rev. 2010; 39: 712
14b Sehnal P, Taylor RJ. K, Fairlamb IJ. S. Chem. Rev. 2010; 110: 824

For excellent reviews on Pd/norbornene-catalyzed multistep reactions, see:

15a Catellani M. Synlett 2003; 298
15b Catellani M, Motti E, Della Cá N. Acc. Chem. Res. 2008; 41: 1512
15c Lautens M, Martins A, Mariampillai B, Lautens M. Top. Curr. Chem. 2010; 292: 1

16a Catellani M, Motti E, Minari M. Chem. Commun. 2000; 157
16b Motti E, Rossetti M, Bocelli G, Catellani M. J. Organomet. Chem. 2004; 689: 3741

17 Wilhelm T, Lautens M. Org. Lett. 2005; 7: 4053
18 Mariampillai B, Alliot J, Li M, Lautens M. J. Am. Chem. Soc. 2007; 129: 15372

19a Lautens M, Piguel S. Angew. Chem. Int. Ed. 2000; 39: 1045
19b Lautens M, Paquin J.-F, Piguel S, Dahlmann M. J. Org. Chem. 2001; 66: 8127
19c Lautens M, Paquin J.-F, Piguel S. J. Org. Chem. 2002; 67: 3972
19d Mitsudo K, Thansandote P, Wilhelm T, Mariampillai B, Lautens M. Org. Lett. 2006; 8: 3939

20a Ferraccioli R, Carenzi D, Catellani M. Tetrahedron Lett. 2004; 45: 6903
20b Ferraccioli R, Giannini C, Molteni G. Tetrahedron: Asymmetry 2007; 18: 1475
20c Ferraccioli R, Forni A. Eur. J. Org. Chem. 2009; 3161

21 Thansandote P, Raemy M, Rudolph A, Lautens M. Org. Lett. 2007; 9: 5255

For Pd-catalyzed intramolecular N-arylation of amines and amides, see:

22a Wolfe JP, Rennels RA, Buchwald SL. Tetrahedron 1996; 52: 7525
22b Yin J, Buchwald SL. Org. Lett. 2000; 2: 1101

23 For a review on the use of secondary alkyl halides in transition-metal-catalyzed cross-coupling reactions, see: Rudolph A, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 2656
24 Candito DA, Lautens M. Org. Lett. 2010; 12: 3312

25a Bressy C, Alberico D, Lautens M. J. Am. Chem. Soc. 2005; 127: 13148
25b Blaszykowski C, Aktoudianakis E, Bressy C, Alberico D, Lautens M. Org. Lett. 2006; 8: 2043
25c Blaszykowski C, Aktoudianakis E, Alberico D, Bressy C, Hulcoop DG, Jafarpour F, Joushaghani A, Laleu B, Lautens M. J. Org. Chem. 2008; 73: 1888
25d Laleu B, Lautens M. J. Org. Chem. 2008; 73: 9164
25e Martins A, Alberico D, Lautens M. Org. Lett. 2006; 8: 4827
25f Martins A, Lautens M. J. Org. Chem. 2008; 73: 8705

For further extension, see also:

25g Jafarpour F, Hazrati H. Adv. Synth. Catal. 2010; 352: 363

26a Gericke KM, Chai DI, Bieler N, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 1447
26b Liu H, El-Salfiti M, Chai DI, Auffret J, Lautens M. Org. Lett. 2012; 14: 3648

27 Gericke KM, Chai DI, Lautens M. Tetrahedron 2008; 64: 6002
28 Liu H, El-Salfiti M, Lautens M. Angew. Chem. Int. Ed. 2012; 51: 9846

29a Alberico D, Lautens M. Synlett 2006; 2969
29b Alberico D, Rudolph A, Lautens M. J. Org. Chem. 2007; 72: 775

30a Rudolph A, Rackelmann N, Lautens M. Angew. Chem. Int. Ed. 2007; 46: 1485
30b Rudolph A, Rackelmann N, Turcotte-Savard M.-O, Lautens M. J. Org. Chem. 2009; 74: 289

31 Mariampillai B, Alberico D, Bidau V, Lautens M. J. Am. Chem. Soc. 2006; 128: 14436

32a Lautens M, Pache S. Org. Lett. 2003; 5: 4827
32b Thansandote P, Gouliaras C, Turcotte-Savard M.-O, Lautens M. J. Org. Chem. 2009; 74: 1791

33 Jafarpour F, Lautens M. Org. Lett. 2006; 8: 3601
34 Catellani M, Motti E. New J. Chem. 1998; 22: 759
35 Catellani M, Chiusoli GP. J. Organomet. Chem. 1985; 286: C13
36 For recent development on the ortho effect, see: Larraufie MH, Maestri G, Beaume A, Derat E, Ollivier C, Fensterbank L, Courillon C, Lacôte E, Catellani M, Malacria M. Angew. Chem. Int. Ed. 2011; 50: 12253
37 Catellani M, Motti E, Baratta S. Org. Lett. 2001; 3: 3611
38 Zhao Y.-B, Mariampillai B, Candito DA, Laleu B, Li M, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 1849
39 For a recent review on α-arylation, see: Bellina F, Rossi R. Chem. Rev. 2010; 110: 1082

For examples on nucleophilic addition of arylpalladium complexes, see:

40a Liu G, Lu X. Org. Lett. 2010; 12: 3336
40b Solé D, Mariani F, Fernandéz I, Sierra MA. J. Org. Chem. 2012; 77: 10272

41 Motti E, Faccini F, Ferrari I, Catellani M, Ferraccioli R. Org. Lett. 2006; 8: 3967

42a Della Cà N, Motti E, Mega A, Catellani M. Adv. Synth. Catal. 2010; 352: 1451
42b Della Cá N, Motti E, Catellani M. Adv. Synth. Catal. 2008; 350: 2513

43 Della Cà N, Sassi G, Catellani M. Adv. Synth. Catal. 2008; 350: 2179
44 The outcome of the reaction with unprotected o-bromo-aniline was completely different: Della Cà N, Maestri G, Malacria M, Derat E, Catellani M. Angew. Chem. Int. Ed. 2011; 50: 12257
45 Ferraccioli R, Carenzi D, Rombolà O, Catellani M. Org. Lett. 2004; 6: 4759
46 Maestri G, Larraufie M.-H, Derat E, Ollivier C, Fensterbank L, Lacôte E, Malacria M. Org. Lett. 2010; 12: 5692
47 Candito DA, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 6713
48 Barluenga J, Aznar F, Valdés C. Angew. Chem. Int. Ed. 2004; 43: 343
49 Thansandote P, Chong E, Feldmann K.-O, Lautens M. J. Org. Chem. 2010; 75: 3495

50a Jiao L, Bach T. J. Am. Chem. Soc. 2011; 133: 12990
50b Jiao L, Herdtweck E, Bach T. J. Am. Chem. Soc. 2012; 134: 14563