(PCy3)2Cl2Ru = CHPh Catalyzed Kharasch additions. Application in a formal olefin carbonylation

Tetrahedron

Volumn 60, Issue 34, 2004, Pages 7391-7396

  Lee, Belinda T ^a   Schrader, Thomas O ^a   Martín Matute, Belén ^a   Kauffman, Christopher R ^a   Zhang, Peng ^a   Snapper, Marc L ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

Carbonylation; Kharasch; Metathesis; Radical

Indexed keywords

ALDEHYDE; ALKENE; BUTENOLIDE; CHLORINE; KETONE; RUTHENIUM;

ACYLATION; ADDITION REACTION; CARBONYLATION; CATALYSIS; CONFERENCE PAPER; HYDROLYSIS; PRIORITY JOURNAL;

EID: 3342889513     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.066     Document Type: Conference Paper

References (48)

1. Colquhoun H.M., Thompson D.J., Twigg M.V. Carbonylation: Direct Synthesis of Carbonyl Compounds. 1991;Plenum, New York
2. Breit B., Seiche W. Synthesis. 2001;1-36
3. Agbossou F., Carpentier J.-F., Mortreux A. Chem. Rev. 95:1995;2485-2506
4. For a related transformation, see: Kreimeramn S., Ryu I., Minakata S., Komatsu M. Org. Lett. 2:2000;389-391. and references cited therein
5. Artman G. III, Weinreb S.M. Org. Lett. 5:2003;1523-1526
6. Copéret C., Negishi E. Org. Lett. 1:1999;165-167
7. Kündig E., Ratni H., Crousse B., Bernardinelle G. J. Org. Chem. 66:2001;1852-1860
8. Zhang Y., Negishi E. J. Am. Chem. Soc. 111:1989;3454-3456
9. Gibson S.E., Stevenazzi A. Angew. Chem. Int. Ed. 42:2003;1800-1810
10. Hicks F.A., Buchwald S.L. J. Am. Chem. Soc. 118:1996;11688-11689. and references cited therein
11. For examples of hydroformylations, see (a) Saraf S.T., Leighton J.L. Org. Lett. 2:2000;3205-3208
12. Krauss I.J., Wang C.C.-Y., Leighton J.L. J. Am. Chem. Soc. 123:2001;11514-11515. and references cited therein
13. For alternative strategies, see: (a) Almtorp G.T., Bachmann T.L., Torssell K.B.G. Acta Chem. Scand. 45:1991;212-215
14. Tsuge O., Kanemasa S., Suga H., Nakagawa N. Bull. Chem. Soc. Jpn. 60:1987;2463-2473
15. Tallarico A., Malnick L.M., Snapper M.L. J. Org. Chem. 64:1999;344-345
16. For similar transformations with Grubbs' metathesis catalysts, see: (b) Simal F., Demonceau A., Noels A.F. Tetrahedron Lett. 40:1999;5689-5693
17. De Clercq B., Verpoort F. J. Mol. Cat. 180:2002;67-76
18. Alcaide B., Almendros P. Chem. Eur. J. 9:2003;1259-1262. and references cited therein. Grubbs' 2nd generation catalyst was not nearly as active in Kharasch additions
19. Kharasch M.S., Jensen E.V., Urry W.H. Science. 102:1945;128
20. Kharasch M.S., Jensen E.V., Urry W.H. J. Am. Chem. Soc. 67:1945;1864-1865
21. Kharasch M.S., Jensen E.V., Urry W.H. J. Am. Chem. Soc. 68:1946;154-155
22. Walling C. Free Radicals in Solution. 1957;Wiley, New York. pp 247-272
23. For transition metal-mediated radical additions, see: (e) Minisci F. Acc. Chem. Res. 8:1975;165-171
24. Iqbal J., Bhatia B., Nayyar N.K. Chem. Rev. 94:1994;519-564
25. Curran D.P. Synthesis. 1988;417-439
26. Curran D.P. Synthesis. 1988;489-513
27. Tsuji J., Sato K., Nagashima H. Chem. Lett. 1981;1169-1170
28. Matsumoto H., Nakano T., Nagai Y. Tetrahedron Lett. 51:1973;5147-5150
29. Lee G.M., Weinreb S.M. J. Org. Chem. 55:1990;1281-1285
30. Feng H., Kavrakova I.K., Pratt D.A., Tellinghuisen J., Porter N.A. J. Org. Chem. 67:2002;6050-6054
31. For a review of transition metal-promoted radical addition reactions, see: (m) Iqbal J., Bhatia B., Nayyar N.K. Chem. Rev. 94:1994;519-564
32. 4 and styrenes, see: (a) Aslam M., Stansbury W., Reiter R., Larkin D. J. Org. Chem. 62:1997;1550-1552
33. Asscher M., Vofsi D. J. Chem. Soc. 1963;3921-3927
34. For the limited systems examined, similar results were obtained for the corresponding tribrominated alkanes (data not shown)
35. Kernan M., Faulkner D.J. J. Org. Chem. 53:1988;2773-2776
36. Cheung A., Snapper M.L. J. Am. Chem. Soc. 124:2002;11584-11585
37. Brohm D., Philippe N., Metzger S., Bhargava A., Muller O., Lieb F., Waldmann H. J. Am. Chem. Soc. 124:2002;13171-13178
38. Demeke D., Forsyth C. J. Org. Lett. 5:2003;991-994
39. De Silva E., Scheuer P.J. Tetrahedron Lett. 21:1980;1611-1614
40. Miyaoka H., Yamanishi M., Kajiwara Y., Yamada Y. J. Org. Chem. 68:2003;3476-3479
41. The cis-trans isomerization of β-acetylacrylic acid under acidic conditions was studied previously, see: Seltzer S., Stevens K.D. J. Org. Chem. 33:1968;2708-2711
42. Walling C., Lepley A.R. J. Am. Chem. Soc. 94:1972;2007-2014
43. For previous reports of compound 7, see: (a) Sato T., Seno M., Asahara T. Seisan Kenkyu. 24:1972;230-233
44. Freidlina R., Kamyshova A.A., Posledova N.N., Chukovskaya E.T., Freidlina R. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya. 1979;392-395
45. Knölker H.-J., Ahrens B., Gonser P., Heininger M., Jones P.G. Tetrahedron. 56:2000;2259-2271
46. Cooper G.K., Dolby L.J. J. Org. Chem. 44:1979;3414-3416
47. Wendler N., Slates H.L. J. Org. Chem. 32:1967;849-851
48. Farrand C., Johnson D.C. J. Org. Chem. 36:1971;3609-3612