Theoretical studies of nickel-catalyzed ring-opening hydroacylation of methylenecyclopropanes and benzaldehydes
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| 024 | 7 | 0 | |a 10.1007/s00894-015-2754-6 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00894-015-2754-6 | ||
| 245 | 0 | 0 | |a Theoretical studies of nickel-catalyzed ring-opening hydroacylation of methylenecyclopropanes and benzaldehydes |h [Elektronische Daten] |c [Fen Wang, Shuhua Zhu, Qingxi Meng, Hongzong Yin] |
| 520 | 3 | |a Density functional theory (DFT) was used to investigate nickel-catalyzed ring-opening hydroacylation of methylenecyclopropanes and benzaldehydes. The results indicated that the Ni-P(n-Bu)3 complex exhibited much more excellent catalysis than the other two complexes (Ni-PMe3 and Ni-P(t-Bu)3). The hydrogen migration was the rate-determining step, and the β-carbon elimination was the chirality-limiting step. The dominant product was a (S,S)- cis ketone. The phosphine ligand P(n-Bu)3 changed the rate-determining step, and greatly decreased the free energies of the rate-determining step and chirality-limiting step. The use of P(n-Bu)3 generally decreased the free energies of the intermediates and transition states. The possible role of P(n-Bu)3 was the transformation of the electron and geometry structures of those intermediates and transition states. Graphical Abstract DFT results indicated that the Ni-P(n-Bu)3 complex exhibited much more excellent catalysis than the other two complexes (Ni-PMe3 and Ni-P(t-Bu)3). The phosphine ligand P(n-Bu)3 changed the rate-determining step, and greatly decreased the free energies of the rate-determining step and chirality-limiting step. | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a Benzaldehyde |2 nationallicence | |
| 690 | 7 | |a DFT |2 nationallicence | |
| 690 | 7 | |a Hydroacylation |2 nationallicence | |
| 690 | 7 | |a Methylenecyclopropane |2 nationallicence | |
| 690 | 7 | |a Nickel |2 nationallicence | |
| 700 | 1 | |a Wang |D Fen |u Department of Chemistry, Taishan University, 271021, Taian, Shandong, People's Republic of China |4 aut | |
| 700 | 1 | |a Zhu |D Shuhua |u College of Chemistry and Material Science, Shandong Agricultural University, 271018, Taian, Shandong, People's Republic of China |4 aut | |
| 700 | 1 | |a Meng |D Qingxi |u College of Chemistry and Material Science, Shandong Agricultural University, 271018, Taian, Shandong, People's Republic of China |4 aut | |
| 700 | 1 | |a Yin |D Hongzong |u College of Chemistry and Material Science, Shandong Agricultural University, 271018, Taian, Shandong, People's Republic of China |4 aut | |
| 773 | 0 | |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/8(2015-08-01), 1-8 |x 1610-2940 |q 21:8<1 |1 2015 |2 21 |o 894 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00894-015-2754-6 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00894-015-2754-6 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Wang |D Fen |u Department of Chemistry, Taishan University, 271021, Taian, Shandong, People's Republic of China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Zhu |D Shuhua |u College of Chemistry and Material Science, Shandong Agricultural University, 271018, Taian, Shandong, People's Republic of China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Meng |D Qingxi |u College of Chemistry and Material Science, Shandong Agricultural University, 271018, Taian, Shandong, People's Republic of China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Yin |D Hongzong |u College of Chemistry and Material Science, Shandong Agricultural University, 271018, Taian, Shandong, People's Republic of China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/8(2015-08-01), 1-8 |x 1610-2940 |q 21:8<1 |1 2015 |2 21 |o 894 | ||