Advances in the synthesis and reactivity of 2-pyranylidene carbene complexes

Chinese Science Bulletin

Volumn 55, Issue 26, 2010, Pages 2915-2923

  Wang, Qi Feng ^a,b   Zhang, Wen Xiong ^a   Lin, Chen ^a   Xi, Zhen Feng ^a  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF CHEMISTRY   (China)

Author keywords

2 pyranylidene carbene complexes; reactivity; synthesis

Indexed keywords

EID: 77957115687     PISSN: 10016538     EISSN: 18619541     Source Type: Journal    
DOI: 10.1007/s11434-010-4047-x     Document Type: Review

References (55)

1. Fischer E O, Maasböl A. On the existence of a tungsten carbonyl carbene complex. Angew Chem Int Ed Engl, 1964, 3: 580-581.
2. Sierra M A. Di- and polymetallic heteroatom stabilized (Fischer) metal carbene complexes. Chem Rev, 2000, 100, 3591-3637.
3. de Meijere A, Schirmer H, Duetsch M. Fischer carbene complexes as chemical multitalents: The incredible range of products from carbenepentacarbonylmetal α,β-unsaturated complexes. Angew Chem Int Ed, 2000, 39: 3964-4002.
4. Barluenga J, Fañanás F J. Metalloxy Fischer carbene complexes: an efficient strategy to modulate their reactivity. Tetrahedron, 2000, 56: 4597-4628.
5. Herndon J W. The use of Fischer carbene complexes for the preparation of five-membered carbocyclic rings. Tetrahedron, 2000, 56: 1257-1280.
6. Aumann R. 1-Metalla-1, 3, 5-hexatrienes and related compounds. Eur J Org Chem, 2000, 17-31.
7. Dötz K H, Jäkel C, Haase W C. Metal glycosylidenes: Novel organometallic tools for C-glycosidation: part 19. organotransition metal modified sugars. J Organomet Chem, 2001, 617/618: 119-132.
8. 2-unsaturated Fischer carbene complexes. J Organomet Chem, 2001, 624: 5-17.
9. Barluenga J, Santamaría J, Tomás M. Synthesis of heterocycles via group VI. Fischer carbene complexes. Chem Rev, 2004, 104: 2259-2283.
10. Barluenga J, Fernández-Rodríguez M A, Aguilar E. Synthesis of heterocycles via group VI Fischer carbene complexes. J Organomet Chem, 2005, 690: 539-587.
11. Gómez-Gallego M, Mancheño M J, Sierra M A. Catalytic transmetalation from group 6 Fischer carbene complexes: An emerging powerful tool in organic synthesis. Acc Chem Res, 2005, 38: 44-53.
12. Zhao Y, Wang J. Nucleophilic addition to C=O and C=N bonds by nucleophiles containing a diazo group. Synlett, 2005, 2886-2892.
13. Ma M, Peng L, Li C, et al. Highly stereoselective [2, 3]-sigmatropic rearrangement of sulfur ylide generated through Cu(I) carbene and sulfides. J Am Chem Soc 2005, 127: 15016-15017.
14. Glorius F. N-heterocyclic carbenes in transition metal catalysis. In: Topics in Organometallic Chemistry. Heidelberg: Springer, 2006.
15. 8)]. Organometallics, 2006, 25: 191-196.
16. Doyle M P. Perspective on dirhodium carboxamidates as catalysts. J Org Chem, 2006, 71: 9253-9260.
17. Zhang L, Sun J, Zhu H, et al. Thermolytic products derived from thermolysis of cycloolefin-coordinated diiron bridging carbene complexes. Organometallics, 2007, 26: 2630-2636.
18. Peng C, Wang Y, Wang J. Palladium-catalyzed cross-coupling of α-diazocarbonyl compounds with arylboronic acids. J Am Chem Soc, 2008, 130: 1566-1567.
19. Gleiter R, Hoffmann R. On stabilizing a singlet methylene. J Am Chem Soc, 1968, 90: 5457-5460.
20. Rees C W, von Angerer E. Pyran-2-ylidene carbene complexes. J Chem Soc Chem Commun, 1972, 420-420.
21. Juneau K N, Hegedus L S, Roepke F W. Synthesis of pentacarbonyl(2, 3-dialkoxycyclopropenylidene)chromium(0), -molybdenum (0), and -tungsten(0) complexes by reaction of metal hexacarbonyls with lithium ethoxyacetylide. J Am Chem Soc, 1989, 111, 4762-4765.
22. Camps F, Moretó J M, Ricart S, et al. Reaction of ethyl diethoxyacrylate with alkynylalkoxycarbene metal (Cr, W) complexes: New procedure for preparation of 6-ethoxy-2H-pyrones. J Chem Soc Chem Commun, 1989, 1560-1562.
23. Camps F, Jordi L, Moretó J M, et al. Reactions of silyl enol ethers With [ethoxy(phenylethynyl)carbene]chromium and tungsten complexes. J Organomet Chem, 1992, 436: 189-198.
24. Jordi L, Moretó J M, Ricart S, et al. Trapping of a carbanionic intermediate in the reaction of alkynylalkoxy carbene metal (Cr) complexes and ethyl diethoxyacrylate. J Organomet Chem, 1993, 444: C28-C30.
25. Jordi L, Camps F, Ricart S, et al. Reaction of ethyl 3, 3-diethoxyacrylate with Fischer alkoxyalkynyl transition metal carbene complexes. J Organomet Chem, 1995, 494: 53-64.
26. Wang S L B, Wulff W D. Inverse-electron-demand Diels-Alder reactions of Fischer carbene complexes: A new and efficient dihydrobenzene synthesis via a retrocycloaddition of chromium hexacarbonyl. J Am Chem Soc, 1990, 112: 4550-4552.
27. 3 durch carbonyl-olefinierung mit triethylamin/chlortrimethylsilan (p 537-540). Chem Ber, 1987, 120: 537-540.
28. Aumann R, Roths K, Läge M, et al. Metathesis of enamines by alkynylcarbene tungsten complexes. formation of aminobenzenes via pyranylidene complexes. Synlett, 1993, 667-669.
29. Aumann R, Kößmeier M, Roths K, et al. Homopyrroles by metal-mediated cycloadditions of (NH)-enamines to alkynylcarbene tungsten complexes via 1-metalla-1, 3, 5-trienes. Synlett, 1994, 1041-1044.
30. Aumann R, Meyer A G, Fröhlich R. Steroid-like ring skeletons by cyclohexadiene annulation to enamines with alkynylcarbene complexes of chromium and tungsten via pyran-2-ylidene complexes. J Am Chem Soc, 1996, 118: 10853-10861.
31. Aumann R, Meyer A G, Fröhlich R. Organic syntheses via transition metal complexes. 86. regioselective [C3 + C2] cyclopentadiene annulation to enamines with alkynylcarbene complexes of chromium and tungsten as novel C3 building blocks. Organometallics, 1996, 15: 5018-5027.
32. Aumann R, Roths K, Jasper B, et al. Organic syntheses via transition metal complexes. 83. 1 cis-1-metalla-1, 3, 5-hexatrienes (butadienylcarbene complexes) of tungsten via ring opening of pyranylidene complexes. Organometallics, 1996, 15: 1257-1264.
33. Yu Z, Aumann R, Fröhlich R, et al. Organic syntheses via transition metal complexes, LXXXVIII 1-metalla-1, 3, 5, 7-octatetraenes from (1-alkynyl) carbene complexes of chromium and tungsten via [6-(1-alkenyl)] pyranylidene complexes. J Organomet Chem, 1997, 541: 187-198.
34. Aumann R, Kößmeier M, Roths K, et al. Organic syntheses via transition metal complexes. Part 103: pyrylium carbonylmetalates and related compounds derived from (1-alkynyl)carbene complexes (M=Cr, W). Tetrahedron, 2000, 56: 4935-4949.
35. Wu H P, Aumann R, Fröhlich R, et al. Stereocontrolled synthesis of angularly fused tricyclic ring systems by means of 1-metalla-1, 3, 5-hexatrienes (M=Cr, W). Chem Eur J, 2002, 8: 910-916.
36. 5M=C(OEt)C≡CPh (M = Cr, W) - efficient chemical synthesis of aromatic polyketides. J Organomet Chem, 2009, 694: 3058-3067.
37. Zheng Z, Yu Z, Luo N, et al. Tautomerism-dependent ring construction of N-heterocyclic compounds from the reactions of 1-alkynyl Fischer carbene complexes and substituted pyrazolinones. J Org Chem, 2006, 71: 9695-9700.
38. Zheng Z, Chen J, Luo N, et al. Efficient demetalation of Fischer alkoxy- and amino-biscarbene complexes of chromium via CO-promoted sulfuration and selenylation. Organometallics, 2006, 25: 5301-5310.
39. Zheng Z, Chen J, Yu Z, et al. Oxidative demetalation of Fischer alkoxy carbene complexes with stoichiometric pyridine N-oxide and NaBH4-promoted demetalation of Fischer iminocarbene complexes with sulfur and selenium. J Organomet Chem, 2006, 691: 3679-3692.
40. Iwasawa N, Shido M, Maeyama K, et al. Novel synthesis of pentacarbonylbenzopyranylidenetungsten(0) complexes and their Diels-Alder reaction with electron-rich alkenes. J Am Chem Soc, 2000, 122: 10226-10227.
41. Kusama H, Shiozawa F, Shido M, et al. Tandem cyclizations of benzopyranylidenetungsten(0) complexes with electron-rich dienes for the stereoselective synthesis of polycyclic carbon skeletons. Chem Lett, 2002, 124-125.
42. Kusama H, Sawada T, Okita A, et al. Synthesis of isochromene esters utilizing 1, 6-addition of nucleophiles to benzopyranylidenetungsten(0) complexes. Org Lett, 2006, 8: 1077-1079.
43. Ohe K, Miki K, Yokoi T, et al. Novel pyranylidene complexes from group 6 transition metals and β-ethynyl α,β-unsaturated carbonyl compounds. Organometallics, 2000, 19: 5525-5528.
44. 5(THF). J Organomet Chem, 2002, 645: 228-234.
45. Szesni N, Weibert B, Fischer H. Alkoxy-substituted group 6 allenylidene complexes - synthesis and properties. Inorg Chim Acta 2006, 359: 617-632.
46. Xi Z. 1-Lithio-1, 3-dienes: Useful building blocks for cyclic compounds. Bull Chem Soc Jpn, 2007, 80: 1021-1032.
47. Xi Z. Reaction chemistry of 1, 4-dilithio-1, 3-diene and 1-lithio-1, 3-diene derivatives. Eur J Org Chem, 2004: 2773-2781.
48. Chen J, Song Q, Wang C Y, et al. Novel cycloaddition of nitriles with monolithio- and dilithiobutadienes. J Am Chem Soc, 2002, 124: 6238-6239.
49. Song Q, Li Z, Chen J, et al. Acyl-lithiation of olefins: Formation of cyclopentenones from 1-lithio-butadienes and CO. Org Lett, 2002, 4: 4627-4629.
50. Song Q, Chen J, Jin X, et al. Highly regio- and stereoselective 1, 1-cycloaddition of carbon monoxide with 1, 4-dilithio-1, 3-dienes. novel synthetic methods for 3-cyclopenten-1-one derivatives. J Am Chem Soc, 2001, 123: 10419-10420.
51. Ubayama H, Xi Z, Takahashi T. Substituent-selective mixed-dihalogenation of unsymmetrical zirconacyclopentadienes. Chem Lett, 1998, 517-518.
52. 6 (M = Cr, Mo, W): Novel synthesis and demetalation reaction. Organometallics, 2008, 27, 3627-3629.
53. Wang Q, Liu L, Lin C, et al. Hydride-induced cleavage of C-O bond in pyran ring of 2-pyranylidene carbene complexes: Mechanism and synthetic application. Dalton Trans, 2009, 10433-10435.
54. Baeza B, Casarrubios L, Gómez-Gallego M, et al. Multicomponent synthesis of pyran-2-ylidene chromium(0) and tungsten(0) Fischer carbene complexes. Organometallics, 2010, 29: 1607-1611.
55. Gilchrist T L, Livingston R, Rees C W, et al. Pyran-2-ylidene carbene complexes. J Chem Soc Perkin Trans 1, 1973, 2535-2539.