Gold(I) N-heterocyclic carbene based initiators for bulk ring-opening polymerization of l-lactide

Journal of Organometallic Chemistry

Volumn 692, Issue 20, 2007, Pages 4259-4269

  Ray, Lipika ^a   Katiyar, Vimal ^a   Barman, Samir ^a   Raihan, Mustafa J ^a   Nanavati, Hemant ^a   Shaikh, Mobin M ^a   Ghosh, Prasenjit ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Gold; Lactide; N Heterocylic carbene; Ring opening polymerization; Silver

Indexed keywords

COMPLEXATION; GOLD COMPOUNDS; MOLECULAR WEIGHT; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL);

GOLD COMPLEXES; N-HETEROCYCLIC CARBENES; POLYLACTIDE POLYMER;

OLEFINS;

EID: 34548020719     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.06.033     Document Type: Article

References (100)

1. Shi Z., and He C. J. Org. Chem. 69 (2004) 3669
2. Reetz M.T., and Sommer K. Eur. J. Org. Chem. (2003) 3485
3. Hashmi A.S.K., Schwarz L., Choi J.-H., and Frost T.M. Angew. Chem., Int. Ed. 39 (2000) 2285
4. Kennedy-Smith J.J., Staben S.T., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 4526
5. Hashmi A.S.K., Frost T.M., and Bats J.W. J. Am. Chem. Soc. 122 (2000) 11553
6. Yao T., Zhang X., and Larock R.C. J. Am. Chem. Soc. 126 (2004) 11164
7. Teles J.H., Brode S., and Chabanas M. Angew. Chem., Int. Ed. 37 (1998) 1415
8. Ito H., Yajima T., Tateiwa J., and Hosomi A. Chem. Commun. (2000) 981
9. Müller T.E., and Pleier A.-K. J. Chem. Soc., Dalton Trans. (1999) 583
10. Shi F., and Deng Y. Chem. Commun. (2001) 443
11. Nolan S.P. Nature 445 (2007) 496
12. Hashmi A.S.K., and Hutchings G.J. Angew. Chem., Int. Ed. 45 (2006) 7897
13. Bender C.F., and Widenhoefer R.A. Org. Lett. (2006) 5303
14. Hoffmann-Röder A., and Krause N. Org. Biol. Chem. 3 (2005) 387
15. Dyker G. Angew. Chem., Int. Ed. 39 (2000) 4237
16. Crabtree R.H. J. Organomet. Chem. 690 (2005) 5451
17. Peris E., and Crabtree R.H. Coord. Chem. Rev. 248 (2004) 2239
18. Cavell K.J., and McGuinness D.S. Coord. Chem. Rev. 248 (2004) 671
19. Crudden C.M., and Allen D.P. Coord. Chem. Rev. 248 (2004) 2247
20. Perry M.C., and Burgess K. Tetrahedron: Asymmetry 14 (2003) 951
21. Schneider S.K., Herrmann W.A., and Herdtweck E.Z. Anorg. Allg. Chem. 629 (2003) 2363
22. Fructos M.R., Belderrain T.R., de Frěmont P., Scott N.M., Nolan S.P., Díaz-Requejo M.M., and Pěrez P.J. Angew. Chem., Int. Ed. 44 (2005) 5284
23. Ray L., Katiyar V., Raihan M.J., Nanavati H., Shaikh M.M., and Ghosh P. Eur. J. Inorg. Chem. (2006) 3724
24. Dorta R., Stevens E.D., Scott N.M., Costabile C., Cavallo L., Hoff C.D., and Nolan S.P. J. Am. Chem. Soc. 127 (2005) 2485
25. Chianese A.R., Li X., Janzen M.C., Faller J.W., and Crabtree R.H. Organometallics 22 (2003) 1663
26. Lee M.-T., and Hu C.-H. Organometallics 23 (2004) 976
27. Boehme C., and Frenking G. Organometallics 17 (1998) 5801
28. Samantaray M.K., Roy D., Patra A., Stephen R., Saikh M., Sunoj R.B., and Ghosh P. J. Organomet. Chem. 691 (2006) 3797
29. Noguchi R., Hara A., Sugie A., and Nomiya K. Inorg. Chem. Commun. 9 (2006) 355
30. Özdemir I., Denizci A., Öztürk H.T., and Çetinkaya B. Appl. Organometal. Chem. 18 (2004) 318
31. Nomiya K., Yamamoto S., Noguchi R., Yokoyama H., Kasuga N.C., Ohyama K., and Kato C. J. Inorg. Biochem. 95 (2003) 208
32. Nomiya K., Takahashi S., and Noguchi R. J. Chem. Soc., Dalton Trans. (2000) 2091
33. Nomiya K., Noguchi R., and Oda M. Inorg. Chim. Acta 298 (2000) 24
34. Nomiya K., Noguchi R., Oshawa K., Tsuda K., and Oda M. J. Inorg. Biochem. 78 (2000) 363
35. Phillips A.D., Gonsalvi L., Romerosa A., Vizza F., and Peruzzini M. Coord. Chem. Rev. 248 (2004) 955
36. McKeage M.J., Maharaj L., and Berners-Price S.J. Coord. Chem. Rev. 232 (2002) 127
37. Berners-Price S.J., Bowen R.J., Fernandes M.A., Layh M., Lesueur W.J., Mahepal S., Mtotywa M.M., Sue R.E., and van Rensberg C.E.J. Inorg. Chim. Acta 358 (2005) 4237
38. Criado J.J., Manzano J.L., and Rodríguez-Fernǎndez E. J. Inorg. Biochem. 96 (2003) 311
39. Caruso F., Rossi M., Tanski J., Pettinari C., and Marchetti F. J. Med. Chem. 46 (2003) 1737
40. Messori L., Abbate F., Marcon G., Orioli P., Fontani M., Mini E., Mazzei T., Carrotti S., O'Connell T., and Zanello P. J. Med. Chem. 43 (2000) 3541
41. Mohamed A.A., Chen J., Bruce A.E., Bruce M.R.M., Bauer J.A.K., and Hill D.T. Inorg. Chem. 42 (2003) 2203
42. Zou J., Taylor P., Dornan J., Robinson S.P., Walkinshaw M.D., and Sadler P.J. Angew. Chem., Int. Ed. 39 (2000) 2931
43. Shaw III C.F. Chem. Rev. 99 (1999) 2589
44. Garrison J.C., and Youngs W.J. Chem. Rev. 105 (2005) 3978
45. Arnold P.L. Heteroatom Chem. 13 (2002) 534
46. Díaz-Requejo M.M., and Pěrez P.J. J. Organomet. Chem. 690 (2005) 5441
47. Ramírez J., Corberǎn R., Sanaǔ M., Peris E., and Fernandez E. Chem. Commun. (2005) 3056
48. Sentman A.C., Csihony S., Waymouth R.M., and Hedrick J.L. J. Org. Chem. 70 (2005) 2391
49. Samantaray M.K., Katiyar V., Roy D., Pang K., Nanavati H., Stephen R., Sunoj R.B., and Ghosh P. Eur. J. Inorg. Chem. (2006) 2975
50. Samantaray M.K., Katiyar V., Pang K., Nanavati H., and Ghosh P. J. Organomet. Chem. 692 (2007) 1672
51. Dechy-Cabaret O., Martin-Vaca B., and Bourissou D. Chem. Rev. 104 (2004) 6147
52. O'Keefe B.J., Hillmyer M.A., and Tolman W.B. J. Chem. Soc., Dalton Trans. (2001) 2215
53. Thakur K.A.M., Kean R.T., Hall E.S., Kolstad J.J., and Munson E.J. Macromolecules 31 (1998) 1487
54. Thakur K.A.M., Kean R.T., Hall E.S., Kolstad J.J., Lindgren T.A., Doscotch M.A., Siepmann J.I., and Munson J.E. Macromolecules 30 (1997) 2422
55. Albertson A.-C., and Varma I.K. Biomacromolecules 4 (2003) 1466
56. Okada M. Prog. Polym. Sci. 27 (2002) 87
57. Kricheldorf H.R. Chemosphere 43 (2001) 49
58. Wang X., Liao K., Quan D., and Wu Q. Macromolecules 38 (2005) 4611
59. Li H., Wang C., Bai F., Yue J., and Woo H.-G. Organometallics 23 (2004) 1411
60. Kim Y., and Verkade J.G. Organometallics 21 (2002) 2395
61. Nijenhuis A.J., Grijpma D.W., and Pennings A.J. Macromolecules 25 (1992) 6419
62. Ejfler J., Kobylka M., Jerzykiewicz L.B., and Sobota P. Dalton Trans. (2005) 2047
63. Jensen T.R., Schaller C.P., Hillmyer M.A., and Tolman W.B. J. Organomet. Chem. 690 (2005) 5881
64. Chisholm M.H., Gallucci J., and Phomphrai K. Chem. Commun. (2003) 48
65. Williams C.K., Breyfogle L.E., Choi S.K., Nam W., Young Jr. V.G., Hillmyer M.A., and Tolman W.B. J. Am. Chem. Soc. 125 (2003) 11350
66. Myers M., Connor E.F., Glauser T., Möck A., Nyce G., and Hedrick J.L. Polym. Sci., Part A: Polym. Chem. 40 (2002) 844
67. Chamberlain B.M., Cheng M., Moore D.R., Ovitt T.M., Lobkovsky E.B., and Coates G.W. J. Am. Chem. Soc. 123 (2001) 3229
68. Dubios Ph., Ropson N., Jěrôme R., and Teyssiě Ph. Macromolecules 29 (1996) 1965
69. Garlotta D. J. Polym. Environ. 9 (2001) 63
70. Brandys M.-C., Jennings M.C., and Puddephatt R.J. J. Chem. Soc., Dalton Trans. (2000) 4601
71. Dave M.P., Patel J.M., Langalia N.A., Shah S.R., and Thaker K.A. J. Indian Chem. Soc. LXII (1985) 386
72. Huynh H.V., Han Y., Ho J.H.H., and Tan G.K. Organometallics 25 (2006) 3267
73. Arnold P.L., Rodden M., Davis M.K., Scarisbrick A.C., Blake A.J., and Wilson C. Chem. Commun. (2004) 1612
74. Bondi A. J. Phys. Chem. 68 (1964) 441
75. Wang H.M.J., and Lin I.J.B. Organometallics 17 (1998) 972
76. Caballero A., Díez-Barra E., Jalǒn F.A., Merino S., and Tejeda J. J. Organomet. Chem. 617-618 (2001) 395
77. Arduengo III A.J., Dias H.V.R., Calabrese J.C., and Davidson F. Organometallics 12 (1993) 3405
78. Çetinkaya B., Dixneuf P., and Lappert M.F. J. Chem. Soc., Dalton Trans. (1974) 1827
79. Liu S.-T., and Reddy K.R. Chem. Soc. Rev. 28 (1999) 315
80. Ku R.-Z., Huang J.-C., Cho J.-Y., Kiang F.-M., Reddy K.R., Chen Y.-C., Lee K.-J., Lee J.-H., Lee G.-H., Peng S.-M., and Liu S.-T. Organometallics 18 (1999) 2145
81. Lee K.M., Lee C.K., and Lin I.J.B. Angew. Chem., Int. Ed. 36 (1997) 1850
82. Bovio B., Calogero S., Wagner F.E., Burini A., and Pietroni B.R. J. Organomet. Chem. 470 (1994) 275
83. Mas-Marzá E., Sanaú M., and Peris E. Inorg. Chem. 44 (2005) 9961
84. Cotton F.A., Wilkinson G., Murillo C.A., and Bochmann M. Advanced Inorganic Chemistry. sixth ed. (1999), John Wiley & Sons, Inc., New York p. 1084
85. Pauling L. The Nature of the Chemical Bond. third ed. (1960), Cornell University Press, Ithaca, NY p. 224, 256
86. de Frémont P., Scott N.M., Stevens E.D., and Nolan S.P. Organometallics 24 (2005) 2411
87. Lee K.M., Wang H.M.J., and Lin I.J.B. J. Chem. Soc., Dalton Trans. (2002) 2852
88. Liu Q.-X., Xu F.-B., Li Q.-S., Zeng X.-S., Leng X.-B., Chou Y.L., and Zhang Z.-Z. Organometallics 22 (2003) 309
89. Ramnial T., Abernethy C.D., Spicer M.D., Mckenzie I.D., Gay I.D., and Clyburne J.A.C. Inorg. Chem. 42 (2003) 1391
90. Tulloch A.A.D., Danopoulos A.A., Winston S., Kleinhenz S., and Eastham G. J. Chem. Soc., Dalton Trans. (2000) 4499
91. Ray L., Shaikh M.M., and Ghosh P. Organometallics 26 (2007) 958
92. de Frémont P., Stevens E.D., Eelman M.D., Fogg D.E., and Nolan S.P. Organometallics 25 (2006) 5824
93. Catalano V.J., and Moore A.L. Inorg. Chem. 44 (2005) 6558
94. de Frémont P., Stevens E.D., Fructos M.R., Diaz-Requejo M.M., Perez P.J., and Nolan S.P. Chem. Commun. (2006) 2045
95. Wang H.M.J., Vasam C.S., Tsai T.Y.R., Chen S.-H., Chang H.H., and Lin I.J.B. Organometallics 24 (2005) 486
96. Baker M.V., Barnard P.J., Berners-Price S.J., Brayshaw S.K., Hickey J.L., Skelton B.W., and White A.H. J. Organomet. Chem. 690 (2005) 5625
97. Lin I.J.B., and Vasam C.S. Can. J. Chem. 83 (2005) 812
98. Tripathi U.M., Bauer A., and Schmidbaur H. J. Chem. Soc., Dalton Trans. (1997) 2865
99. Lee C.K., Lee K.M., and Lin I.J.B. Organometallics 21 (2002) 10
100. Wang H.M.J., Chen C.Y.L., and Lin I.J.B. Organometallics 18 (1999) 1216