Alkynedicobalt Complexes in γ-Carbonyl Cations and Cycloheptynedicobalt Complexes

James R. Green

doi:10.1055/s-0031-1290486

Synlett, Table of Contents

Synlett 2012; 23(9): 1271-1282
DOI: 10.1055/s-0031-1290486

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Alkynedicobalt Complexes in γ-Carbonyl Cations and Cycloheptynedicobalt Complexes

James R. Green*

Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, N9B 3P4, Canada, Fax: +1(519)9737098 Email: jgreen@uwindsor.ca

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Abstract

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Abstract

This Account describes our work on highly electrophilic γ-carbonyl cations featuring propargyldicobalt cations, cycloheptynedicobalt complexes, and the interconnection between the two systems.

1 Introduction

2 γ-Carbonyl Cations via Iron Allyl Cations

3 γ-Carbonyl Cations via Propargyldicobalt Cations

3.1 Synthesis of Velloziolide

3.2 Synthesis of Microstegiol

4 Synthesis of Cycloheptynedicobalt Complexes

4.1 Synthesis via γ-Carbonyl Cations

4.2 Cycloheptynedicobalt Complexes via [4+3] Cycloaddition Reactions

4.3 Cycloheptynedicobalt Complexes via Ring-Closing Metathesis

4.4 Cycloaddition Reactions on Cycloheptynedicobalt Complexes

4.5 Cycloheptynedicobalt Complexes via Intramolecular Nicholas Reactions

5 Dehydrotropylium Ion Co₂(CO)₆ Complex

6 Final Comments

Key words

carbocation - alkyne complexes - transition-metal - Umpolung - ring closure

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References

References
1 Premparee P, Raviroongit S, Thebtaranonth Y. J. Org. Chem. 1983; 48: 3553

2a Orsini F. Synthesis 1985; 500
2b Corey EJ, Kuwajima I. Tetrahedron Lett. 1972; 13: 487

3a Sheffy FK, Godschalx JP, Stille JK. J. Am. Chem. Soc. 1984; 106: 4833
3b Bonini C, Chiummiento L, De Bonis M, Funicello M, Lupattelli P, Pandolfo R. Tetrahedron: Asymmetry 2006; 17: 2919
3c Zultanski SL, Fu GC. J. Am. Chem. Soc. 2011; 133: 15362

4a Trost BM, Li C. J. Am. Chem. Soc. 1994; 116: 3167
4b Zhang C, Lu X. Synlett 1995; 645
4c Smith S, Fu GC. J. Am. Chem. Soc. 2009; 131: 14231
4d Lu X, Zhang C, Xu Z. Acc. Chem. Res. 2001; 34: 535

5a Pd: Tsuji J, Ueno H, Kobayashi Y, Okumoto H. Tetrahedron Lett. 1981; 21: 2573
5b Nemoto T, Fukuda T, Matsumoto T, Hitomi T, Hamada Y. Adv. Synth. Catal. 2005; 347: 1504
5c Mo: Trost BM, Lautens M. Organometallics 1983; 2: 1687
5d Zhang Y, Liebeskind L. J. Am. Chem. Soc. 2005; 127: 11258
5e Ir: Baeza A, Casas J, Nájera C, Sansano JM. J. Org. Chem. 2006; 71: 3837

6a Kuhn O, Mayr H. Angew. Chem. Int. Ed. 1999; 38: 343
6b Ma S, Yu S, Peng Z, Guo H. J. Org. Chem. 2006; 71: 9865

7a Bambal R, Kemmitt RD. W. J. Chem. Soc., Chem. Commun. 1988; 734
7b Harrington PA, Kerr MA. Tetrahedron Lett. 1997; 38: 5949
7c Yu M, Pagenkopf BL. Tetrahedron 2005; 61: 321

8a Whitesides TH, Arhart RW, Slaven RW. J. Am. Chem. Soc. 1973; 95: 5792
8b Dieter JW, Zhong L, Nicholas KM. Tetrahedron Lett. 1987; 28: 5415

9a Green JR, Carroll MK. Tetrahedron Lett. 1991; 32: 1141
9b Zhuo T, Green JR. Tetrahedron Lett. 1993; 34: 4497
9c Charlton MA, Green JR. Can. J. Chem. 1997; 75: 965

10a Enders D, Finkam M. Synlett 1993; 401
10b Enders D, Jandeleit B, von Berg S. Synlett 1997; 421

11 De Koning H, Hiemstra H, Moolenaar MJ, Speckamp WN. Eur. J. Org. Chem. 1998; 1729

12a Green JR, Donaldson WA In Encyclopedia of Inorganic Chemistry . Vol. 4. Lukehart CM. Wiley; Chichester: 1994: 1735
12b Knölker HJ, Heber J, Mahler CH. Synlett 1992; 1002

For recent reviews dedicated to the Nicholas reaction:
13a Shea KM In Name Reactions for Homologations . Li JJ. Wiley; Hoboken: 2009. Part 1, 284
13b Diaz DD, Betancort JM, Martin VS. Synlett 2007; 343
13c Teobald BJ. Tetrahedron 2002; 58: 4133
13d Green JR. Curr. Org. Chem. 2001; 5: 809

For reviews covering Nicholas reactions in part, see:

13e Fletcher AJ, Christie SD. R. J. Chem. Soc., Perkin Trans. 1 2000; 1657
13f Welker ME. Curr. Org. Chem. 2001; 5: 785
13g Müller TJ. J. Eur. J. Org. Chem. 2001; 2021
13h Omae I. Appl. Organomet. Chem. 2007; 21: 318
13i Bromfield KM, Gradén H, Ljungdahl N, Kann N. J. Chem. Soc., Dalton Trans. 2009; 5052

14 Vizniowski CS, Green JR, Breen TL, Dalacu AV. J. Org. Chem. 1995; 60: 7496
15 Jacobi PA, Buddhu SC, Fry D, Rajeswari S. J. Org. Chem. 1997; 62: 2894
16 Mayr H, Kempf B, Ofial AR. Acc. Chem. Res. 2003; 36: 66
17 Pinto AC, Gonçalves ML. A, Filho RB, Neszmely A, Lukacs G. J. Chem. Soc. 1982; 293
18 Marco JL, Rodriguez B. An. Quim. 1985; 81: 80
19 Green JR, Tjeng AA. J. Org. Chem. 2009; 74: 7411

20a Ulubelen A, Topçu G, Tan N, Lin L.-J, Cordell GA. Phytochemistry 1992; 31: 2419
20b Topçu G, Altiner EN, Gozcu S, Halfon B, Aydogmus Z, Pezzuto JM, Zhou B.-N, Kingston DG. I. Planta Med. 2003; 69: 464
20c Kabouche A, Boutaghane N, Kabouche Z, Seguin E, Tillequin F, Benlabed K. Filoterapia 2005; 76: 450
20d Ulubelen A, Oksuz S, Kolak U, Bozok-Johansson C, Celik C, Voelter W. Planta Med. 2000; 66: 458

21 Taj RA, Abhayawardhana A, Green JR. Synlett 2009; 292
22 Taj RA, Green JR. J. Org. Chem. 2010; 75: 8258
23 See for example: Fraga BM. Nat. Prod. Rep. 2011; 28: 1580
24 For a review, see: Green JR. Eur. J. Org. Chem. 2008; 6053
25 Schreiber SL, Sammakia T, Crowe WE. J. Am. Chem. Soc. 1986; 108: 3128

For reviews see:
26a Hopf H, Grunenberg J In Strained Hydrocarbons . Dodziuk H. Wiley-VCH; Weinheim: 2009
26b Krebs A, Wilke J. Top. Curr. Chem. 1983; 109: 189

27a Al-Omari M, Banert K, Hagedorn M. Angew. Chem. Int. Ed. 2006; 45: 309
27b Okuyama T, Fujita M. Acc. Chem. Res. 2005; 38: 679
27c Hosokawa S, Isobe M. Synlett 1996; 352

28a Schore NE, Najdi SD. J. Org. Chem. 1987; 52: 5296
28b Isobe M, Yenjai C, Tanaka S. Synlett 1994; 916
28c Hosokawa S, Isobe M. Synlett 1995; 1179

29a Nakamura T, Matsui T, Tanino K, Kuwajima I. J. Org. Chem. 1997; 62: 3032
29b Tanino K, Onuki K, Asano K, Miyashita M, Nakamura T, Takahashi Y, Kuwajima I. J. Am. Chem. Soc. 2003; 125: 1498

30 Takano S, Sugihara T, Ogasawara K. Synlett 1992; 70
31 Green JR. Chem. Commun. 1998; 1751
32 Patel MM, Green JR. Chem. Commun. 1999; 509
33 Lu Y, Green JR. Synlett 2001; 243
34 Mohamed AB. Ph.D. Dissertation. University of Windsor; Canada: 2005

35a Tanino K, Shimizu T, Miyama M, Kuwajima I. J. Am. Chem. Soc. 2000; 122: 6116
35b Tanino K, Kondo F, Shimizu T, Miyashita M. Org. Lett. 2002; 4: 2217
35c Mitachi K, Yamamoto T, Kondo F, Shimizu T, Miyashita M, Tanino K. Chem. Lett. 2010; 39: 630

36 For an additional Michael reaction based synthesis, see: Inaba K, Tanaka J, Iwasawa N. Chem. Lett. 2007; 36: 474

For [4+2] cycloadditions not involving a Nicholas reaction process, see:
37a Iwasawa N, Sakurada F, Iwamoto M. Org. Lett. 2000; 2: 871
37b Iwasawa N, Inaba K, Nakayama S, Aoki M. Angew. Chem. Int. Ed. 2005; 44: 7447

38 Green JR. Synlett 2001; 353

39a Burlison JA, Gray JM, Young DG. J. Tetrahedron Lett. 2001; 42: 5363
39b Young DG. J, Burlison JA, Peters U. J. Org. Chem. 2003; 68: 3494

40 Mohamed AB, Green JR, Masuda J. Synlett 2005; 1543
41 Sugihara T, Yamaguchi M, Nishizawa M. Chem. Eur. J. 2001; 7: 1589
42 Mohamed AB, Green JR. Chem. Commun. 2003; 2936
43 Ding Y. M. Sc. Thesis. University of Windsor; Canada: 2004
44 Iwasawa N, Ooi I, Inaba K, Takaya J. Angew. Chem. Int. Ed. 2010; 49: 7534
45 Ding Y, Green JR. Synlett 2005; 271

46a Hosokawa S, Isobe M. Tetrahedron Lett. 1998; 39: 2609
46b Takai S, Ploypradith P, Hamajima A, Kira K, Isobe M. Synlett 2002; 588
46c Isobe M, Yenjai C, Tanaka S. Synlett 2002; 916

47 Kira K, Tanda H, Hamajima A, Baba T, Takai S, Isobe M. Tetrahedron 2002; 58: 6485

48a Djudjevic S, Green JR. Org. Lett. 2007; 9: 5505
48b Djurdjevic S, Yang F, Green JR. J. Org. Chem. 2010; 75: 8241

49 Vorogushin AV, Predeus AV, Wulff WD, Hansen H.-J. J. Org. Chem. 2003; 68: 5826

50a Suri JT, Vu T, Hernandez A, Congdon J, Singaram B. Tetrahedron Lett. 2002; 43: 3649
50b Cordes DB, Nguyen TM, Kwong TJ, Suri JT, Luibrand RT, Singaram B. Eur. J. Org. Chem. 2005; 5289

51 Viaud MC, Rollin P. Synthesis 1990; 130
52 Kolodziej I, Green JR. Synlett 2011; 2397

53a Padmanabhan S, Nicholas KM. Tetrahedron Lett. 1982; 23: 2555
53b Shibuya S, Isobe M. Tetrahedron 1998; 54: 6667
53c Álvaro E, de la Torre MC, Sierra MA. Org. Lett. 2003; 5: 2381

54 DiMartino J, Green JR. Tetrahedron 2006; 62: 1402

55a Amiralaei S, Green JR. Chem. Commun. 2008; 4971
55b Amiralaei S, Gauld J, Green JR. Chem. Eur. J. 2011; 17: 4157