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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Xu, Zheng-yang Yu, Hai-zhu Fu, Yao Su, Wei Jiang, Yuan-ye |
| Description | Author Affiliation: Xu ZY ( Hefei National Laboratory for Physical Sciences at the Microscale, iChEM, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.); Jiang YY ( Hefei National Laboratory for Physical Sciences at the Microscale, iChEM, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.); Su W ( Hefei National Laboratory for Physical Sciences at the Microscale, iChEM, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.); Yu HZ ( Department of Chemistry and Centre for Atomic Engineering of Advanced Materials, Anhui University, Hefei, 230601, China. yuhaizhu@ahu.edu.cn.); Fu Y ( Hefei National Laboratory for Physical Sciences at the Microscale, iChEM, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China. fuyao@ustc.edu.cn.) |
| Abstract | Cu-catalyzed alkylboration of alkenes with bis(pinacolato)diboron $((Bpin)_{2})$ and alkyl halides provides a ligand-controlled regioselectivity-switchable method for the construction of complex boron-containing compounds. Here, we employed DFT methods to elucidate the mechanistic details of this reaction and the origin of the different regioselectivity induced by Xantphos and Cy-Xantphos. The calculation results reveal that the catalytic cycle mainly proceeds through the migratory insertion of alkenes on Cu-Bpin complex, the oxidative addition of alkyl halides, and the reductive elimination of a C−C bond. Meanwhile, the rate- determining step is the oxidative addition of alkyl halides and the regioselectivity-determining step is the migratory insertion of alkenes. The bulky cyclohexyl group of Cy-Xantphos facilitates the approach of the substituents of alkenes to Bpin in the migratory insertion step and thus leads to the Markovnikov products. The less bulky phenyl group on Xantphos prefers keeping the substituents of alkenes away from the Bpin moiety in the migratory insertion step and thus results in anti-Markovnikov products. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 41 |
| Volume Number | 22 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2016-10-04 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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