Investigation of the aqueous transmetalation of π-allylpalladium with Indium: Some theoretical and experimental evidence about the nature of allylindium intermediates

Letters in Organic Chemistry

Volumn 3, Issue 2, 2006, Pages 98-102

  Fontana, Gianfranco ^a,b   Savona, Giuseppe ^a   Ferrante, Francesco ^a  

^a UNIVERSITY OF PALERMO   (Italy)

^b Parco d'Orleans II   (Italy)

Author keywords

Allyl indium; Allyl palladium; Allylation; Umpolung

Indexed keywords

EID: 34247164494     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806775224305     Document Type: Article

References (25)

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25. Computational methods: All calculations were performed by using electronic structure theory at the density functional (DFT) and MP2 levels. In the DFT approach the three parameters hybrid functional B3LYP, mixing Becke's exchange with the non-local correlation functional provided by Lee, Parr and Yang, was utilized. The cc-pvdz basis set was used for the light atoms, while the cc-pvdz-PP small-core relativistic effective core potential correlation consistent basis set was used for the indium atom. This ECP takes into account the 28 inner electrons of indium; the outer electrons are described by a valence basis set whose contraction scheme is [14s11p6d]/(4s3p2d). All geometries were optimised by checking the Hessian matrix and the enthalpies were calculated by adding the zero-point and thermal correction to the SCF energies. The Gaussian 03 package was used for all calculations [Frish, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheesenan, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; 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, K.; Knox, J. E.; Hratchan, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, I.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Canmi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannemberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K. Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, L. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Gonzales, C.; Pople, J. A. Gaussian 03 Revision A.1. Gaussian, Inc., Pittsburgh Pa, 2003].