Chem. J. Chinese Universities ›› 2018, Vol. 39 ›› Issue (7): 1475.doi: 10.7503/cjcu20180117
• Physical Chemistry • Previous Articles Next Articles
FANG Sheng, WANG Meiyan*(), LIU Jingjing, LIU Jingyao
Received:
2018-02-09
Online:
2018-07-10
Published:
2018-06-14
Contact:
WANG Meiyan
E-mail:mywang858@jlu.edu.cn
Supported by:
CLC Number:
TrendMD:
FANG Sheng, WANG Meiyan, LIU Jingjing, LIU Jingyao. Reaction Mechanism of Nickel Complex Catalyzed Isomerization of N-Allylamides†[J]. Chem. J. Chinese Universities, 2018, 39(7): 1475.
Fig.1 Energy profiles calculated for C—H bond activation by Ni(PPh3)2(1Ni) to form complex 3Ni^ The calculated free energies relative to 1Ni+N-allyl-4-methylbenzamide are given in kJ/mol.
Fig.2 Energy profiles calculated for isomerization of π-allyl complex 3Ni via the π-allyl mechanism to generate E isomer^ The calculated free energies relative to 1Ni+N-allyl-4-methylbenzamide are given in kJ/mol.
Fig.3 Energy profiles calculated for isomerization of π-allyl complex 3Ni via the σ-allyl mechanism to generate E isomer^ The H atom bonded to Ni is directed outwards(A) and inwards(B). The calculated free energies relative to 1Ni+N-allyl-4-methylbenzamide are given in kJ/mol.
Fig.4 Energy profiles calculated for isomerization of π-allyl complex 3'Ni via the π-allyl(A) and σ-allyl(B) mechanism^ The calculated free energies relative to 1Ni+N-allyl-4-methylbenzamide are given in kJ/mol.
Fig.5 Structures and energies of the rate-determining intermediate 2ZNi and five lowest transition states on the energy profiles to generate Z isomer^The calculated free energies relative to 1Ni+N-allyl-4-methylbenzamide are given in kJ/mol.
Fig.6 Structures and energies of the rate-determining intermediate 2Pd and transition states TS34aPd and TS34ZaPd on the energy profiles to generate E and Z isomer^The calculated free energies relative to 1Pd+N-allyl-4-methylbenzamide are given in kJ/mol.
Fig.7 Energy decomposition analyses of the energy barriers(kJ/mol) from rate-determining intermediates 2M to transition states TS34aM^ a. The energy of Ni; b. the energy of Pd; c. the energy difference of Ni and Pd.
Fig.8 Structures and energies(kJ/mol) of two rate-determining transition states TS34a-tBu and TS34Za-tBu(A) for reactant with R=tBu (relative to 1Ni+N-allyl-pivaloylamide), as well as TS34a and TS34Za(B) for reactant with R=p-MeC6H4 (relative to 1Ni+N-allyl-4-methylbenzamide)
[1] | Van Santen R.A.,van Leeuwen P. W. N. M.,Moulijn J A.,Averill B. A., Catalysis: An Integrated Approach, Elsevier,Amsterdam, 1999 |
[2] | Mirza-Aghayan M., Boukherroub R., Bolourtchian M., Hoseini M., Tabar-Hydar K., J. Organomet. Chem., 2003, 678, 1—4 |
[3] | Donohoe T. J., O'Riordan T. J. C., Rosa C. P., Angew. Chem. Int. Ed., 2009, 48, 1014—1017 |
[4] | Krompiec S., Krompiec M., Penczek H., Ignasiak R., Coord. Chem. Rev., 2008, 252, 1819—1841 |
[5] | Escoubet S., Gastaldi S., Bertrand M.,Eur. J. Org. Chem., 2005, 3855—3873 |
[6] | Kramer S., Mielby J., Buss K., Kasama T., Kegnæs S., Chem. Cat. Chem., 2017, 9, 2930—2934 |
[7] | Wu Q., Wang L., Jin R., Kang C., Bian Z., Du Z., Ma X., Guo H., Gao L.,Eur. J. Org. Chem., 2016, 5415—5422 |
[8] | Kocen A. L., Brookhart M., Daugulis O., Chem. Commun., 2017, 53, 10010—10013 |
[9] | Zhuo L. G., Yao Z. K., Yu Z. X., Org. Lett., 2013, 15, 4634—4637 |
[10] | Stille J.K., Becker Y., J. Org. Chem., 1980, 45, 2139—2145 |
[11] | Sergeyev S. A., Hesse M., Helvetica Chimica Acta, 2003, 86, 750—755 |
[12] | Yamada H., Sodeoka M., Shibasaki M., J. Org. Chem., 1991, 56, 4569—4574 |
[13] | Zacuto M. J., Xu F., J. Org. Chem., 2007, 72, 6298—6300 |
[14] | Krompiec S., Pigulla M., Kuz'nik N., Krompiec M., Marciniec B., Chadyniak D., Kasperczyk J., J. Mol. Cat. A: Chem., 2005, 225, 91—101 |
[15] | Krompiec S., Pigulla M., Bieg T., Szczepankiewicz W., Kuz'nik N., Krompiec M., Kubicki M., J. Mol. Cat. A: Chem., 2002, 189, 169—185 |
[16] | Krompiec S., Pigulla M., Szczepankiewicz W., Bieg T., Kuznik N., Leszczynska-Sejda K., Kubicki M., Borowiak T., Tetrahedron Lett., 2001, 42, 7095—7098 |
[17] | Neugnot B., Cintrat J. C., Rousseau B., Tetrahedron, 2004, 60, 3575—3579 |
[18] | Nakanishi S., Otsuji Y., Itoh K., Hayashi N., Bull. Chem. Soc. Jpn., 1990, 63, 3595—3600 |
[19] | Couture A., Deniau E., Grandclaudon P., Lebrun S., Tetrahedron Lett., 1996, 37, 7749—7752 |
[20] | Naito T., Yuumoto Y., Kiguchi T., Ninomiya I., J. Chem. Soc., Perkin Trans., 1996, 1, 281—288 |
[21] | Wang L., Liu C., Bai R., Pan Y., Lei A., Chem. Commun., 2013, 49, 7923—7925 |
[22] | Kozuch S., Shaik S., J. Am. Chem. Soc., 2017, 11, 4075—4086 |
[23] | Zhang X., Tutkowski B., Oliver A., Helquist P., Wiest O., ACS Catal., 2018, 8, 1740—1747 |
[24] | Frisch M.J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J. A. Jr., Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J., Brothers E., Kudin K. N., Staroverov V. N., Keith T., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam J. M., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth G. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas O., Foresman J. B., Ortiz J. V., Cioslowski J., Fox D. J., Gaussian 09, Revision E. 01, Gaussian Inc., Wallingford CT, 2013 |
[25] | Becke A. D., Phys. Rev.A, 1988, 38, 3098—3100 |
[26] | Lee C., Yang W., Parr R. G., Phys. Rev. B, 1988, 37, 785—789 |
[27] | Becke A. D., J. Chem.Phys., 1993, 98, 5648—5652 |
[28] | Hay P. J., Wadt W. R., J. Chem. Phys., 1985, 82, 270—283 |
[29] | Hay P. J., Wadt W. R., J. Chem. Phys., 1985, 82, 299—310 |
[30] | Ehlers A. W., Böhme M., Dapprich S., Gobbi A., Höllwarth A., Jonas V., Köhler K. F., Stegmann R., Veldkamp A., Frenking G., Chem. Phys. Lett., 1993, 208, 111—114 |
[31] | Fukui K., Acc. Chem.Res., 1981, 14, 363—368 |
[32] | Zhao Y., Truhlar D. G., J. Chem. Phys., 2006, 125, 194101 |
[33] | Dolg M., Wedig U., Stoll H., Preuss H., J. Chem.Phys., 1987, 86, 866—872 |
[34] | Andrae D., Haeussermann U., Dolg M., Stoll H., Preuss H., Theor. Chem. Acc., 1990, 77, 123—141 |
[35] | Marenich A. V., Cramer C. J., Truhlar D. G., J. Phys. Chem. B, 2009, 113, 6378—6396 |
[36] | Kozuch S., Shaik S., Acc. Chem. Res., 2011, 44, 101—110 |
[37] | Xie H., Kuang J., Wang L., Li Y., Huang L., Fan T., Lei Q., Fang W., Organometallics, 2017, 36, 3371—3381 |
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