A DFT computational study of the mechanism of butadiene carbonylation catalyzed by palladium complexes

References

• Vasapollo , G , Somasunderam , A , Ali , BE and Alper , H . 1994 . Tetrahedron Lett. , 35 : 6203 J. F. Knifton, J. Catal. 60, 27 (1979); J. Tsuji, Acc. Chem. Res. 6, 5 (1973)
   Google Scholar
• Beller , M and Bolm , C . 1998 . Transition Metals for Organic Synthesis , Weinheim : Wiley-VCH . J. Tsuji, Palladium Reagents and Catalysts (John Wiley & Sons Ltd., Chichester, 1995)
   Google Scholar
• Tsuji , J , Sato , K and Okumoto , H . 1984 . J. Org. Chem. , 49 : 1341
   Google Scholar
• Matsuzaka , H , Hiroe , Y , Iwasaki , M , Ishii , Y , Koyasu , Y and Hidai , M . 1988 . J. Org. Chem. , 53 : 3832 S.-I. Murahashi, Y. Imada, Y. Taniguchi, and S. Higashiura, J. Org. Chem. 58, 1538 (1993); A. Yamamoto, Bull. Chem. Soc. Jpn. 68, 433 (1995)
   Google Scholar
• Okano , T , Okabe , N and Kiji , J . 1992 . Bull. Chem. Soc. Jpn. , 65 : 2589
   Google Scholar
• Murahashi , S-I , Imada , Y and Nishimura , K . 1994 . Tetrahedron , 50 : 453
   Web of Science ®Google Scholar
• Neibecker , D , Poirier , J and Tkatchenko , I . 1989 . J. Org. Chem. , 54 : 2459 M. C. Bonnet, J. Coombes, B. Manzano, D. Neibecker, and I. Tkatchenko, J. Mol. Catal. 52, 263 (1989)
   Google Scholar
• Tsuji , J , Kiji , J , Imamura , S and Morikawa , M . 1964 . J. Am. Chem. Soc. , 86 : 4350 J. F. Knifton, J. Organomet. Chem. 188, 223 (1980); M. Sakamoto, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn. 69, 1065 (1996); R. Naigre and H. Alper, J. Mol. Catal. A: Chem. 111, 11 (1996); T. Satoh, M. Ikeda, Y. Kushino, M. Miura, and M. Nomura, J. Org. Chem. 62, 2662 (1997)
   Web of Science ®Google Scholar
• Beller , M , Krotz , A and Baumann , W . 2002 . Adv. Synt. Catal. , 334 : 517
   Google Scholar
• Kiss , G . 2001 . Chem. Rev. , 101 : 3435
   PubMed Web of Science ®Google Scholar
• Bertleff , W , Maerkl , R , Kuehn , G , Panitz , P and Kummer , R . 1988 . : 0267497 (BASF AG), EP ; Chem. Abstr. 109, 057058 (1988); R. Maerkl, W. Bertleff, H. J. Wilfinger, G. Schuch, W. Harder, G. Kuehn, and P. Panitz (BASF AG), US Patent 4,894,474 (1990); Chem. Abstr. 110, 192257 (1989); R. Jackstell, M. Gomez, A. Frisch, H. Klein, K. Selvakumar, A. Zapf, A. Spannemberg, D. Rötger, O. Briel, R. Karch, and M. Beller, Angew. Chem. Int. Ed. 41, 986 (2002); F. Vollmüller, W. Mägerlein, S. Kein, J. Krause, and M. Beller, Adv. Synt. Catal. 343, 29 (2001); F. Vollmüller, S. Kein, J. Krause, W. Mägerlein, and M. Beller, Eur. J. Inorg. Chem. 1825 (2000)
   Google Scholar
• Tsuji , J and Hosaka , S . 1964 . J. Am. Chem. Soc. , 86 : 4350 S. Hosaka, and J. Tsuji, Tetrahedron 27, 3821 (1971); J. Tsuji, Y. Mori, and M. Hara, Tetrahedron 28, 3721 (1972)
   Web of Science ®Google Scholar
• Reetz , MT , Breinbauer , R and Wanninger , K . 1996 . Tetrahedron Lett. , 37 : 4499 M. Beller, H. Fischer, K. Kühlein, C.-P. Reisinger, and W. A. Herrmann, J. Organomet. Chem. 520, 257 (1996); M. T. Reetz, and E. Westermann, Angew. Chem., Int. Ed. 39, 165 (2000)
   Web of Science ®Google Scholar
• Klingelhöfer , S , Heitz , W , Greiner , A , Oestreich , S , Förster , S and Antonietti , M . 1997 . J. Am. Chem. Soc. , 119 : 10116 S. V. Ley, C. Ramarao, RS. Gordon, A, B. Holmes, A. J. Morrison, I. F. McConvey, I. M. Shirley, S. C. Smith, and M. D. Smith, Chem. Commun. 1134 (2002); D. E. Bergbreiter, P. L. Osbun, and C. Li, Org. Lett. 4, 737 (2002)
   Web of Science ®Google Scholar
• Rahim , EH , Kamounah , FS , Frederiksen , J and Christense , JB . 2001 . Nano. Lett. , 1 : 499
   Web of Science ®Google Scholar
• Kogan , V , Aizenshtat , Z , Popovitz-Biro , R and Neumann , R . 2002 . Org. Lett. , 4 : 3529
   PubMed Web of Science ®Google Scholar
• Amatore , C and Jutand , A . 1999 . J. Organomet. Chem. , 576 : 254
   Web of Science ®Google Scholar
• Amatore , C , Azzabi , M and Jutand , A . 1989 . J. Organomet. Chem. , 363 : C41 E. Duňach, D. Franco, and S. Olivero, Eur. J. Org. Chem. 1605 (2003); E.-I. Neghishi, AO. King, and N. Okukado, J. Org. Chem. 42, 1821 (1977); JF. Fauvarque, and A. Jutand, Bull. Soc. Chim. Fr. 765 (1976), MR. Mason, and JG. Verkade, Organometallics 11, 2212 (1992)
   Google Scholar
• Knifton , JF . 1978 . J. Am. Oil Chem. Soc. , 55 : 496 D. M. Fenton, J. Org. Chem. 38, 3192 (1973); K. Bittler, N. Kutepow, D. Neubauer, and H. Reis, Angew. Chem., Int. Ed. Engl. 7, 329 (1968); O. L. Kalia, O. N. Temkin, I. G. Mechriakova, and P. M. Flid, Dokl. Akad. Nauk SSSR 199, 1321 (1971); T. E. Kron, Mi. I. Terekhova, Yu. G. Noskov, and E. S. Petrov, Russ. J. Gen. Chem. 68, 681 (1998)
   Google Scholar
• Petrova , NE , Noskov , YuG , Terekhova , MI and Petrov , ES . 1993 . Russ. J. Gen. Chem. , 63 : 478 K. Itoh, M. Miura, and M. Nomura, Tetrahedron Lett. 33, 3569 (1992); H. Yoshida, N. Sugita, K. Kudo, and Y. Takezaki, Bull. Chem. Soc. Jpn. 49, 2245 (1976); J. F. Knifton, J. Org. Chem. 41, 2885 (1976); G. Yu. Noskov. M. I. Terekhova, and E. S. Petrov, Kinet. Catal. 34, 898 (1993); G. Cavinato and L. Toniolo J. Mol. Catal. 10, 161 (1981); K. Kudo, Y. Oida, K. Mitsihashi, S. Mori, K. Komatsu, and N. Sugita, Bull. Chem. Soc. Jpn. 69, 1337 (1996)
   Google Scholar
• Grushin , VA . 1996 . Chem. Rev. , 96 : 2011 J. Tsuji and K. Ohno, J. Am. Chem. Soc. 90, 94 (1968); F. Cariati, R. Ugo, and F. Bonati, Inorg. Chem. 7, 1128 (1966)
   Google Scholar
• Vavasori , A and Toniolo , L . 1996 . J. Mol. Catal. A: Chem. , 110 : 13
   Google Scholar
• Fenton , DM . 1973 . J. Org. Chem. , 38 : 3192 G. Cavinato and L. Toniolo, J. Mol. Catal. 10, 161 (1981); G. Cavinato and L. Toniolo, J. Mol. Catal. 6, 111 (1979); D. Kruis, N. Ruiz, MD. Janssen, J. Boersma, C. Claver, and G. Koten, Inorg. Chem. Commun. 1, 295 (1998); Yu. G. Noskov, and ES. Petrov, Kinet. Katal. 35, 672 (1993)
   Google Scholar
• Cotton , AF , Faller , JW and Musco , A . 1967 . Inorg. Chem. , 6 : 179
   Google Scholar
• Hierso , J-C , Fihri , A , Amardeil , R and Meunier , P . 2003 . Organometallics , 22 : 4490
   Web of Science ®Google Scholar
• Drent , E , Broekhoven , JAM and Budzelaar , PHM . 1996 . Applied Homogeneous Catalysis with Organometallic Compounds , Vol. 1 , 333 New York : VCH . E. Drent and P. H. M. Budzelaar, Chem. Rev. 96, 663 (1996); K. Kudo, Y. Oida, K. Mitsihasi, S. Mori, K. Komatsu, and N. Sugita, Bull. Chem. Soc. Jpn. 69, 1337 (1996)
   Google Scholar
• Knight , JG and Tchabanenko , K . 2002 . Tetrahedron , 58 : 6659
   Google Scholar
• Becke , AD . 1993 . J. Chem. Phys. , 98 : 5648
   Web of Science ®Google Scholar
• Godbout , N , Salahub , DR , Andzelm , J and Wimmer , E . 1992 . Can. J. Chem. , 70 : 560
   Web of Science ®Google Scholar
• Carvajal , MA , Miscione , GP , Novoa , JJ and Bottoni , A . 2005 . Organometallics , 24 : 2086
   Google Scholar
• Cancès , MT , Mennucci , B and Tomasi , J . 1997 . J. Chem. Phys. , 107 : 3032 M. Cossi, V. Barone, B. Mennucci, and J. Tomasi, Chem. Phys. Lett. 286, 253 (1998); B. Mennucci and J. Tomasi, J. Chem. Phys. 106, 5151 (1997)
   Web of Science ®Google Scholar
• Frisch , MJ , Trucks , GW , Schlegel , HB , Scuseria , GE , Robb , MA , Cheeseman , JR , Montgomery , JA , Vreven , T Jr , Kudin , KN , Burant , JC , Millam , JM , Iyengar , SS , Tomasi , J , Barone , V , Mennucci , B , Cossi , M , Scalmani , G , Rega , N , Petersson , GA , Nakatsuji , H , Hada , M , Ehara , M , Toyota , K , Fukuda , R , Hasegawa , J , Ishida , M , Nakajima , T , Honda , Y , Kitao , O , Nakai , H , Klene , M , Li , X , Knox , JE , Hratchian , HP , Cross , JB , Bakken , V , Adamo , C , Jaramillo , J , Gomperts , R , Stratmann , RE , Yazyev , O , Austin , AJ , Cammi , R , Pomelli , C , Ochterski , JW , Ayala , PY , Morokuma , K , Voth , GA , Salvador , P , Dannenberg , JJ , Zakrzewski , VG , Dapprich , S , Daniels , AD , Strain , MC , Farkas , O , Malick , DK , Rabuck , AD , Raghavachari , K , Foresman , JB , Ortiz , JV , Cui , Q , Baboul , AG , Clifford , S , Cioslowski , J , Stefanov , BB , Liu , G , Liashenko , A , Piskorz , P , Komaromi , I , Martin , RL , Fox , DJ , Keith , T , Al-Laham , MA , Peng , CY , Nanayakkara , A , Challacombe , M , Gill , PMW , Johnson , B , Chen , W , Wong , MW , Gonzalez , C and Pople , JA . 2004 . Gaussian 03, Revision C.02 , Wallingford CT : Gaussian, Inc. .
   Google Scholar