{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T06:03:13Z","timestamp":1790402593913,"version":"4.1.0"},"reference-count":156,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2010,5,28]],"date-time":"2010-05-28T00:00:00Z","timestamp":1275004800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2010,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The mechanism of a recently discovered intramolecular Heck\u2010type coupling of oximes with aryl halides (\n                    <jats:italic>Angew. Chem. Int. Ed.<\/jats:italic>\n                    <jats:bold>2007<\/jats:bold>\n                    ,\n                    <jats:italic>46<\/jats:italic>\n                    , 6325) was systematically studied by using density functional methods enhanced with a polarized continuum solvation model. The overall catalytic cycle of the reaction was found to consist of four steps: oxidative addition, migratory insertion, \u03b2\u2010H elimination, and catalyst regeneration, whereas an alternative base\u2010promoted C\uf8ffH activation pathway was determined to be less favorable. Migratory insertion was found to be the rate determining step in the catalytic cycle. The apparent activation barrier of migratory insertion of the (\n                    <jats:italic>E<\/jats:italic>\n                    )\u2010oxime was +20.5\u2005kcal\u2009mol\n                    <jats:sup>\u22121<\/jats:sup>\n                    , whereas the barrier of (\n                    <jats:italic>Z<\/jats:italic>\n                    )\u2010oxime was as high as +32.7\u2005kcal\u2009mol\n                    <jats:sup>\u22121<\/jats:sup>\n                    . However, (\n                    <jats:italic>Z<\/jats:italic>\n                    )\u2010oxime could isomerize to form the more active (\n                    <jats:italic>E<\/jats:italic>\n                    )\u2010oxime with the assistance of K\n                    <jats:sub>2<\/jats:sub>\n                    CO\n                    <jats:sub>3<\/jats:sub>\n                    , so that both the (\n                    <jats:italic>E<\/jats:italic>\n                    )\u2010 and (\n                    <jats:italic>Z<\/jats:italic>\n                    )\u2010oxime substrates could be transformed to the desired product. Our calculations also indicated that the\n                    <jats:italic>Z<\/jats:italic>\n                    product was predominant in the equilibrium of the isomerization of the imine double bond, which constituted the reason for the good\n                    <jats:italic>Z<\/jats:italic>\n                    \u2010selectivity observed for the reaction. Furthermore, we examined the difference between the intermolecular Heck\u2010type reactions of imines and of olefins. It was found that in the intermolecular Heck\u2010type coupling of imines, the apparent activation barrier of migratory insertion was as high as +35\u2005kcal\u2009mol\n                    <jats:sup>\u22121<\/jats:sup>\n                    , which should be the main obstacle of the reaction. The analysis also revealed the main problem for the intermolecular Heck\u2010type reactions of imines, which was that the breaking of a C\uf8feN \u03c0 bond was much more difficult than the breaking of a C\uf8feC \u03c0 bond. After systematic examination of a series of substituted imines, (\n                    <jats:italic>Z<\/jats:italic>\n                    )\u2010\n                    <jats:italic>N<\/jats:italic>\n                    \u2010amino imine and\n                    <jats:italic>N\u2010<\/jats:italic>\n                    acetyl imine were found to have relatively low barriers of migratory insertion, so that they might be possible substrates for intermolecular Heck\u2010type coupling.\n                  <\/jats:p>","DOI":"10.1002\/asia.200900744","type":"journal-article","created":{"date-parts":[[2010,5,1]],"date-time":"2010-05-01T08:17:08Z","timestamp":1272701828000},"page":"1475-1486","source":"Crossref","is-referenced-by-count":31,"title":["Heck\u2010Type Reactions of Imine Derivatives: A DFT Study"],"prefix":"10.1002","volume":"5","author":[{"given":"Zhe","family":"Li","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yao","family":"Fu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Song\u2010Lin","family":"Zhang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qing\u2010Xiang","family":"Guo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lei","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2010,5,28]]},"reference":[{"key":"e_1_2_7_1_2","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19941062307"},{"key":"e_1_2_7_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199423791"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9903048"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00665-2"},{"key":"e_1_2_7_5_2","first-page":"143","volume":"27","author":"Wang Z.\u2010T.","year":"2007","journal-title":"Chin. 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Nonetheless they do not enter the catalytic cycle; see Figure\u2005S1 in the Supporting Information."},{"key":"e_1_2_7_86_2","unstructured":"\u00a0"},{"key":"e_1_2_7_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00029a004"},{"key":"e_1_2_7_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00029a005"},{"key":"e_1_2_7_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp990092i"},{"key":"e_1_2_7_90_2","unstructured":"\u00a0"},{"key":"e_1_2_7_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19991018)111:20<3201::AID-ANGE3201>3.0.CO;2-Z"},{"key":"e_1_2_7_91_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19991018)38:20<3018::AID-ANIE3018>3.0.CO;2-F"},{"key":"e_1_2_7_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011306o"},{"key":"e_1_2_7_93_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200390091"},{"key":"e_1_2_7_93_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390123"},{"key":"e_1_2_7_94_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11244-005-3814-4"},{"key":"e_1_2_7_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/om050703v"},{"key":"e_1_2_7_96_2","unstructured":"\u00a0"},{"key":"e_1_2_7_97_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462327"},{"key":"e_1_2_7_97_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462327"},{"key":"e_1_2_7_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja070657l"},{"key":"e_1_2_7_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/om000002s"},{"key":"e_1_2_7_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja052047w"},{"key":"e_1_2_7_101_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja056800x"},{"key":"e_1_2_7_102_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200602773"},{"key":"e_1_2_7_102_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200602773"},{"key":"e_1_2_7_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja062509l"},{"key":"e_1_2_7_104_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja067144j"},{"key":"e_1_2_7_105_2","unstructured":"\u00a0"},{"key":"e_1_2_7_106_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja056165v"},{"key":"e_1_2_7_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja071034a"},{"key":"e_1_2_7_108_2","unstructured":"This indicates that the inversion of amino palladium is more difficult than alkyl amines. The activation barrier for the inversion of BnN(OMe)Me is +12.2\u2005kcal\u2009mol\u22121 see:"},{"key":"e_1_2_7_109_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)89468-X"},{"key":"e_1_2_7_110_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cplett.2005.10.014"},{"key":"e_1_2_7_111_2","unstructured":"\u00a0"},{"key":"e_1_2_7_112_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00964a029"},{"key":"e_1_2_7_113_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00755a022"},{"key":"e_1_2_7_114_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00403a050"},{"key":"e_1_2_7_115_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo952124d"},{"key":"e_1_2_7_116_2","doi-asserted-by":"publisher","DOI":"10.1039\/b202005j"},{"key":"e_1_2_7_117_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0104375"},{"key":"e_1_2_7_118_2","unstructured":"Note that the Heck coupling of electron\u2010rich olefins has a regioselectivity problem between \u03b1 and \u03b2 positions of the olefin. With the emphasis on the difference between imine and olefin we only discuss the pathway leads to the \u00e2\u2010substituted olefin. For experimental studies see:"},{"key":"e_1_2_7_119_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.19970030823"},{"key":"e_1_2_7_120_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0450861"},{"key":"e_1_2_7_121_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja028755o"},{"key":"e_1_2_7_122_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0315098"},{"key":"e_1_2_7_123_2","doi-asserted-by":"publisher","DOI":"10.1021\/om800114a"},{"key":"e_1_2_7_124_2","doi-asserted-by":"publisher","DOI":"10.1021\/om900674y"},{"key":"e_1_2_7_125_2","unstructured":"The reaction free energy of C\uf8feN addition by benzene of (E)\u2010N\u2010acetyl ethanimine is \u221212.0\u2005kcal\u2009mol\u22121 indicating that a weak C\uf8feN bond can decrease the activation barrier of migratory insertion. However the activation barrier is also controlled by other factors. For example the apparent activation barriers of (E)\u2010N\u2010phenyl ethanimine and (E)\u2010N\u2010amino ethanimine are +37.5\u2005kcal\u2009mol\u22121and +34.1\u2005kcal\u2009mol\u22121 respectively whereas the free energies of C\uf8feN addition by benzene are \u22120.2\u2005kcal\u2009mol\u22121and +6.8\u2005kcal\u2009mol\u22121 respectively."},{"key":"e_1_2_7_126_2","unstructured":"Gaussian 03 Revision C.02 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman J.\u2005A. Montgomery \u2005Jr. T. Vreven K.\u2005N. Kudin J.\u2005C. Burant J.\u2005M. Millam S.\u2005S. Iyengar J. Tomasi V. Barone B. Mennucci M. Cossi G. Scalmani N. Rega G.\u2005A. Petersson H. Nakatsuji M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai M. Klene X. Li J.\u2005E. Knox H.\u2005P. Hratchian J.\u2005B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. 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