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DOI | 10.1126/science.aat2299 |
Enantiodivergent Pd-catalyzed C-C bond formation enabled through ligand parameterization | |
Zhao, Shibin1,2; Gensch, Tobias3; Murray, Benjamin1,2; Niemeyer, Zachary L.3; Sigman, Matthew S.3; Biscoe, Mark R.1,2 | |
2018-11-09 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 362期号:6415页码:670-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | Despite the enormous potential for the use of stereospecific cross-coupling reactions to rationally manipulate the three-dimensional structure of organic molecules, the factors that control the transfer of stereochemistry in these reactions remain poorly understood. Here we report a mechanistic and synthetic investigation into the use of enantioenriched alkylboron nucleophiles in stereospecific Pd-catalyzed Suzuki cross-coupling reactions. By developing a suite of molecular descriptors of phosphine ligands, we could apply predictive statistical models to select or design distinct ligands that respectively promoted stereoinvertive and stereoretentive cross-coupling reactions. Stereodefined branched structures were thereby accessed through the predictable manipulation of absolute stereochemistry, and a general model for the mechanism of alkylboron transmetallation was proposed. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000450474500037 |
WOS关键词 | CROSS-COUPLING REACTIONS ; MOLECULAR-ORBITAL METHODS ; TERTIARY BORONIC ESTERS ; SUZUKI-MIYAURA REACTION ; ASSEMBLY-LINE SYNTHESIS ; BASIS-SETS ; ORGANOMETALLIC CHEMISTRY ; ASYMMETRIC CATALYSIS ; ORGANIC-MOLECULES ; PHOSPHINE-LIGANDS |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/200036 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.CUNY City Coll, Dept Chem, 160 Convent Ave, New York, NY 10031 USA; 2.CUNY, Grad Ctr, PhD Program Chem, 365 Fifth Ave, New York, NY 10016 USA; 3.Univ Utah, Dept Chem, 315 South 1400 East, Salt Lake City, UT 84112 USA |
推荐引用方式 GB/T 7714 | Zhao, Shibin,Gensch, Tobias,Murray, Benjamin,et al. Enantiodivergent Pd-catalyzed C-C bond formation enabled through ligand parameterization[J]. SCIENCE,2018,362(6415):670-+. |
APA | Zhao, Shibin,Gensch, Tobias,Murray, Benjamin,Niemeyer, Zachary L.,Sigman, Matthew S.,&Biscoe, Mark R..(2018).Enantiodivergent Pd-catalyzed C-C bond formation enabled through ligand parameterization.SCIENCE,362(6415),670-+. |
MLA | Zhao, Shibin,et al."Enantiodivergent Pd-catalyzed C-C bond formation enabled through ligand parameterization".SCIENCE 362.6415(2018):670-+. |
条目包含的文件 | 条目无相关文件。 |
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