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DOI | 10.1126/science.aas8961 |
Heterobiaryl synthesis by contractive C-C coupling via P(V) intermediates | |
Hilton, Michael C.1; Zhang, Xuan1; Boyle, Benjamin T.1; Alegre-Requena, Juan V.1; Paton, Robert S.1,2; McNally, Andrew1 | |
2018-11-16 | |
发表期刊 | SCIENCE |
ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 362期号:6416页码:799-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA; England |
英文摘要 | Heterobiaryls composed of pyridine and diazine rings are key components of pharmaceuticals and are often central to pharmacological function. We present an alternative approach to metal-catalyzed cross-coupling to make heterobiaryls using contractive phosphorus C-C couplings, also termed phosphorus ligand coupling reactions. The process starts by regioselective phosphorus substitution of the C-H bonds para to nitrogen in two successive heterocycles; ligand coupling is then triggered via acidic alcohol solutions to form the heterobiaryl bond. Mechanistic studies imply that ligand coupling is an asynchronous process involving migration of one heterocycle to the ipso position of the other around a central pentacoordinate P(V) atom. The strategy can be applied to complex drug-like molecules containing multiple reactive sites and polar functional groups, and also enables convergent coupling of drug fragments and late-stage heteroarylation of pharmaceuticals. |
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:000450488500046 |
WOS关键词 | CORRELATED MOLECULAR CALCULATIONS ; LATE-STAGE FUNCTIONALIZATION ; MEDICINAL CHEMISTS TOOLBOX ; GAUSSIAN-BASIS SETS ; ORBITAL METHODS ; PYRIDINES ; PHOSPHINES ; CATALYST ; SOLVENT ; MODEL |
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/200089 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA; 2.Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England |
推荐引用方式 GB/T 7714 | Hilton, Michael C.,Zhang, Xuan,Boyle, Benjamin T.,et al. Heterobiaryl synthesis by contractive C-C coupling via P(V) intermediates[J]. SCIENCE,2018,362(6416):799-+. |
APA | Hilton, Michael C.,Zhang, Xuan,Boyle, Benjamin T.,Alegre-Requena, Juan V.,Paton, Robert S.,&McNally, Andrew.(2018).Heterobiaryl synthesis by contractive C-C coupling via P(V) intermediates.SCIENCE,362(6416),799-+. |
MLA | Hilton, Michael C.,et al."Heterobiaryl synthesis by contractive C-C coupling via P(V) intermediates".SCIENCE 362.6416(2018):799-+. |
条目包含的文件 | 条目无相关文件。 |
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