Transition-metal-catalyzed carbonylation of allenes with carbon monoxide and thiols

Tetrahedron

Volumn 62, Issue 26, 2006, Pages 6355-6360

  Kajitani, Minako ^a   Kamiya, Ikuyo ^b   Nomoto, Akihiro ^a   Kihara, Nobuhiro ^c   Ogawa, Akiya ^a  

^a Osaka Prefecture University   (Japan)

^b NARA WOMEN'S UNIVERSITY   (Japan)

^c KANAGAWA UNIVERSITY   (Japan)

Author keywords

Allene; Carbon monoxide; Carbonylative thiolation; Copolymerization; Thiol

Indexed keywords

ALLENE DERIVATIVE; CARBON MONOXIDE; CYCLOHEXYL 1 CYCLONONENE 1 CARBOTHIOLATE; CYCLOHEXYL 2 CYCLONONENE 1 CARBOTHIOLATE; THIOL DERIVATIVE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; POLYMERIZATION; PRIORITY JOURNAL;

EID: 33646787142     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.04.039     Document Type: Article

References (71)

1. Cornils B., and Herrmann W.A. Applied Homogeneous Catalysis with Organometallic Compounds Vol. 1 (2002), Wiley-VCH, Weinheim pp 1-194
2. Tsuji J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis (2000), Wiley, Chichester, UK pp 227-297
3. Colquhoun H.M., Thompson D.J., and Twigg M.V. Carbonylation: Direct Synthesis of Carbonyl Compounds (1991), Plenum, New York, NY
4. Murai S., and Sonoda N. Angew. Chem., Int. Ed. Engl. 18 (1979) 837
5. Matsuda I., Ogiso A., Sato S., and Izumi Y. J. Am. Chem. Soc. 111 (1989) 2332
6. Ojima I., Inagallina P., Donovan R.J., and Clos N. Organometallics 10 (1991) 38
7. Ojima I., Donovan R.J., and Shay W.R. J. Am. Chem. Soc. 114 (1992) 6580
8. Marciniec B. In: Cornils B., and Herrmann W.A. (Eds). Applied Homogeneous Catalysis with Organometallic Compounds Vol. 1 (2002), Wiley-VCH, Weinheim 506-508
9. Ojima I. In: Patai S., and Rappoport Z. (Eds). The Chemistry of Organic Silicon Compounds (1989), Wiley, Chichester, UK 1518-1520 Part 2
10. Pino P., and Magri R. Chim. Ind. (Milan) 34 (1952) 511
11. Riegel H.J., and Hoberg H. J. Organomet. Chem. 260 (1984) 121
12. Ozawa F., Nakano M., Aoyama I., Yamamoto T., and Yamamoto A. J. Chem. Soc., Chem. Commun. (1986) 382
13. Lin Y.-S., and Yamamoto A. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 (2002), Wiley, New York, NY 2389-2395 For carbonylative amination of allenes, see:
14. Grigg R., Monteith M., Sridharan V., and Terrier C. Tetrahedron 54 (1998) 3885
15. Zhou D.-Y., Yoneda E., Onitsuka K., and Takahashi S. Chem. Commun. (2002) 2868
16. Tsuji J., and Nogi T. J. Am. Chem. Soc. 88 (1966) 1289
17. Stille J.K., and Hines L.F. J. Am. Chem. Soc. 92 (1970) 1798
18. Li J.-H., Tang S., and Xie Y.-X. J. Org. Chem. 70 (2005) 477
19. Ali B.E., and Alper H. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis Vol. 1 (2004), Wiley-VCH, Weinheim 113-132
20. Schmalz H.-G., and Geis O. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 (2002), Wiley, New York, NY 2377-2389 For carbonylative alkoxylation of allenes, see:
21. Alper H., Hartstok F.W., and Despeyroux B. J. Chem. Soc., Chem. Commun. (1984) 905
22. Zhou D.-Y., Yoneda E., Onitsuka K., and Takahashi S. Chem. Commun. (2002) 2868
23. Lathbury D., Peter V., and Gallagher T. Tetrahedron Lett. 27 (1986) 6009
24. Yoneda E., Zhang S.-W., Onitsuka K., and Takahashi S. Tetrahedron Lett. 42 (2001) 5459
25. Hegedus L.L., and McCabe R.W. Catalyst Poisoning (1984), Marcel Dekker, New York, NY
26. Kuniyasu H., Ogawa A., Miyazaki S., Ryu I., Kambe N., and Sonoda N. J. Am. Chem. Soc. 113 (1991) 9796
27. Kuniyasu H., Ogawa A., Sato K., Ryu I., Kambe N., and Sonoda N. J. Am. Chem. Soc. 114 (1992) 5902
28. Ogawa A., Ikeda T., Kimura K., and Hirao T. J. Am. Chem. Soc. 121 (1999) 5108
29. Ogawa A., Takeba M., Kawakami J., Ryu I., Kambe N., and Sonoda N. J. Am. Chem. Soc. 117 (1995) 7564
30. Kawakami J., Takeba M., Kamiya I., Sonoda N., and Ogawa A. Tetrahedron 59 (2003) 6559
31. Ogawa A., Kawakami J., Mihara M., Ikeda T., Sonoda N., and Hirao T. J. Am. Chem. Soc. 119 (1997) 12380
32. Kawakami J., Mihara M., Kamiya I., Takeba M., Ogawa A., and Sonoda N. Tetrahedron 59 (2003) 3521
33. Kondo T., Uenoyama S., Fujita K., and Mitsudo T. J. Am. Chem. Soc. 121 (1999) 482
34. Ogawa A., Kawakami J., Sonoda N., and Hirao T. J. Org. Chem. 61 (1996) 4161
35. Palladium acetate with phosphine was reported to exhibit a catalytic activity toward the thiocarbonylation of allenes, see:
36. Xiao W.-J., Vasapollo G., and Alper H. J. Org. Chem. 63 (1998) 2609
37. Xiao W.-J., and Alper H. J. Org. Chem. 64 (1999) 9646
38. Transition-metal-catalyzed heterofunctionalization of allenes was reported. For reviews, see:
39. Yamamoto Y., and Radhakrishnan U. Chem. Soc. Rev. (1999) 199
40. Zimmer R., Dinesh C.U., Nandanan E., and Khan F.A. Chem. Rev. 100 (2000) 3067
41. Mandai T. In: Krause N., Stephen A., and Hashimi K. (Eds). Modern Allene Chemistry Vol. 2 (2004), Wiley-VCH, Weinheim 925-972
42. Transition-metal-catalyzed addition of heteroatom compounds was reported. [B-B]:
43. Ishiyama T., Kitano T., and Miyaura N. Tetrahedron Lett. 39 (1998) 2357
44. Yang F.-Y., and Cheng C.-H. J. Am. Chem. Soc. 123 (2001) 761 [B-Si]:
45. Suginome M., Ohmori Y., and Ito Y. Synlett (1999) 1567
46. Suginome M., Ohmori Y., and Ito Y. J. Organomet. Chem. 611 (2000) 403
47. Suginome M., Ohmura T., Miyake Y., Mitani S., Ito Y., and Murakami M. J. Am. Chem. Soc. 125 (2003) 11174
48. Chang K.-J., Rayabarapu D.K., Yang F.-Y., and Cheng C.-H. J. Am. Chem. Soc. 127 (2005) 126 [B-Sn]:
49. Onozawa S., Hatanaka Y., and Tanaka M. Chem. Commun. (1999) 1863 [Si-Si]:
50. Watanabe H., Saito M., Sutou N., and Nagai Y. J. Chem. Soc., Chem. Commun. (1981) 617
51. Watanabe H., Saito M., Sutou N., Kishimoto K., Inose J., and Nagai Y. J. Organomet. Chem. 225 (1982) 343 [Si-Sn]:
52. Mitchell T.N., and Schneider U. J. Organomet. Chem. 407 (1991) 319 [Sn-Sn]:
53. Killing H., and Mitchell T.N. Organometallics 3 (1984) 1318 [Sn-Ge]:
54. Mitchell T.N., Schneider U., and Fröhling B. J. Organomet. Chem. 384 (1990) C53 [Se-Se]:
55. 2NH]:
56. Al-Masum M., Meguro M., and Yamamoto Y. Tetrahedron Lett. 38 (1997) 6071
57. Besson L., Goré J., and Cazes B. Tetrahedron Lett. 36 (1995) 3857 [ROH]:
58. Rutjes F.P.J.T., Kooistra T.M., Hiemstra H., and Schoemaker H.E. Synlett (1998) 192 [RCOOH]:
59. Al-Masum M., and Yamamoto Y. J. Am. Chem. Soc. 120 (1998) 3809 [RP(O)H]:
60. Zhao C.-Q., Han L.-B., and Tanaka M. Organometallics 19 (2000) 4196 [Ge-H, Sn-H]:
61. Ichinose Y., Oshima K., and Utimoto K. Bull. Chem. Soc. Jpn. 61 (1988) 2693 [Se-H]:
62. Ogawa A., Kudo A., and Hirao T. Tetrahedron Lett. 39 (1998) 5213
63. In this reaction, reductive elimination selectively takes place after insertion of CO. Indeed, the formation of allylic sulfides (derived from allylic platinum species by the reductive elimination) was not detected at all.
64. This platinum-catalyzed carbonylative thiolation involves two key platinum species, i.e., H-Pt-SR (I) and H-Pt-C(O)SR (II). Allenes may insert preferentially into Pt-X bonds (X=H, SR, and C(O)SR) by the order of Pt-C(O)SR>H-Pt>Pt-SR, although the real reason to explain this tendency should wait for further detailed mechanistic study. On the other hand, the regioselectivity of the catalysis suggests terminal attachment of the bulkier platinum moiety at the insertion stage. Also, the stability between allylic platinum species (formed by terminal attack) and vinylic platinum species (formed by inner attack) may contribute to the reaction course. Cf.
65. Sugoh K., Kuniyasu H., Sugae T., Ohtaka A., Takai Y., Tanaka A., Machino C., Kambe N., and Kurosawa H. J. Am. Chem. Soc. 123 (2001) 5108
66. Hirai T., Kuniyasu H., and Kambe N. Chem. Lett. 33 (2004) 1148
67. Hirai T., Kuniyasu H., and Kambe N. Tetrahedron Lett. 46 (2005) 117
68. Kacker S., and Sen A. J. Am. Chem. Soc. 119 (1997) 10028
69. Osakada K., Choi J.-C., and Yamamoto T. J. Am. Chem. Soc. 119 (1997) 12390
70. Osakada K., Takenaka Y., Choi J.-C., Yamaguchi I., and Yamamoto T. J. Polym. Sci., Part A: Polym. Chem. 38 (2000) 1505
71. Takenaka Y., and Osakada K. Macromol. Chem. Phys. 202 (2001) 3571