Reactivity and Selectivity in Catalytic Reactions of Enoldiazoacetamides. Assessment of Metal Carbenes as Intermediates

作者: Hadi Arman , Michael P. Doyle , Yongming Deng , Changcheng Jing

DOI: 10.1021/ACS.ORGANOMET.6B00648

关键词: Polymer chemistryCycloadditionPhotochemistryRutheniumChemistryRhodiumTransition metal carbene complexCyclopropeneReactivity (chemistry)CatalysisCarbene

摘要: Catalyst effectiveness for metal carbene formation and reactions has been surveyed using N-(tert-butyl)-3-[(tert-butyldimethylsilyl)oxy]-2-diazo-N-(4-chlorobenzyl)but-3-enamide in the of products from both intramolecular C–H insertion aromatic cycloaddition. Both are indicators intermediates, this system provides a means to assess catalysts formation. Donor–acceptor cyclopropene production reactant enoldiazoacetamide monitored its formation, independently formed also used Catalysts rhodium(II), copper(I), silver(I), Pd(II), cationic Au(I), Zn(II) convert donor–acceptor which serves as resting state intermediate carbene, derivative give same ratios cycloaddition products. copper(II) ruthenium(II...

参考文章(54)
Alan Ford, Hugues Miel, Aoife Ring, Catherine N. Slattery, Anita R. Maguire, M. Anthony McKervey, Modern Organic Synthesis with α-Diazocarbonyl Compounds Chemical Reviews. ,vol. 115, pp. 9981- 10080 ,(2015) , 10.1021/ACS.CHEMREV.5B00121
Yongming Deng, Changcheng Jing, Michael P. Doyle, Dinitrogen extrusion from enoldiazo compounds under thermal conditions: synthesis of donor–acceptor cyclopropenes Chemical Communications. ,vol. 51, pp. 12924- 12927 ,(2015) , 10.1039/C5CC05006E
Fang Wei, Chuanling Song, Yudao Ma, Ling Zhou, Chen-Ho Tung, Zhenghu Xu, Gold carbene chemistry from diazo compounds Science Bulletin. ,vol. 60, pp. 1479- 1492 ,(2015) , 10.1007/S11434-015-0874-0
Guichun Fang, Xihe Bi, Silver-catalysed reactions of alkynes: recent advances Chemical Society Reviews. ,vol. 44, pp. 8124- 8173 ,(2015) , 10.1039/C5CS00027K
Xin Cui, Xue Xu, Li-Mei Jin, Lukasz Wojtas, X. Peter Zhang, Stereoselective radical C–H alkylation with acceptor/acceptor-substituted diazo reagents via Co(II)-based metalloradical catalysis Chemical Science. ,vol. 6, pp. 1219- 1224 ,(2015) , 10.1039/C4SC02610A
Jianbo Wang, Bei Chen, Jian Bao, Electronic Effects of Rh(II)-Mediated Carbenoid Intramolecular C−H Insertion: A Linear Free Energy Correlation Study Journal of Organic Chemistry. ,vol. 63, pp. 1853- 1862 ,(1998) , 10.1021/JO971747J
Xinfang Xu, Peter J. Zavalij, Michael P. Doyle, A donor-acceptor cyclopropene as a dipole source for a silver(I) catalyzed asymmetric catalytic [3+3]-cycloaddition with nitrones. Chemical Communications. ,vol. 49, pp. 10287- 10289 ,(2013) , 10.1039/C3CC46415F
Huw M. L. Davies, Baihua Hu, Elie Saikali, Paul R. Bruzinski, Carbenoid versus Vinylogous Reactivity in Rhodium(II)-Stabilized Vinylcarbenoids Journal of Organic Chemistry. ,vol. 59, pp. 4535- 4541 ,(1994) , 10.1021/JO00095A031
Albert Padwa, David J. Austin, Alan T. Price, Mark A. Semones, Michael P. Doyle, Marina N. Protopopova, William R. Winchester, Andrea Tran, Ligand effects on dirhodium(II) carbene reactivities. Highly effective switching between competitive carbenoid transformations Journal of the American Chemical Society. ,vol. 115, pp. 8669- 8680 ,(1993) , 10.1021/JA00072A021