| Title | Cu(I)-Catalyzed Synthesis of Furan-Substituted Allenes by Use of Conjugated Ene-yne Ketones as Carbene Precursors |
| Authors | Hu, Fangdong Xia, Ying Ma, Chen Zhang, Yan Wang, Jianbo |
| Affiliation | Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China. Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China. |
| Keywords | OXIDATION/1,2-ALKYNYL MIGRATION/CYCLIZATION CASCADE ALPHA-DIAZOCARBONYL COMPOUNDS TERMINAL ALKYNES SYNTHESIS METAL-CATALYZED REACTIONS H BOND FUNCTIONALIZATION MIGRATORY INSERTION N-TOSYLHYDRAZONES ORGANIC-SYNTHESIS DIAZO-COMPOUNDS ACTIVATION |
| Issue Date | 2016 |
| Publisher | JOURNAL OF ORGANIC CHEMISTRY |
| Citation | JOURNAL OF ORGANIC CHEMISTRY.2016,81,(8),3275-3285. |
| Abstract | The synthesis of furan-substituted allenes using conjugated ene-yne ketones as carbene source has been developed. For this reaction, bases play vital roles in controlling the reaction pathways, allowing for access to two types of allene products through trapping of different electrophiles. Mechanistically, the catalytic procedure generated a Cu(I) (2-furyl)carbene intermediate, which is subsequently followed by a migratory insertion process to afford nucleophilic organo copper species. The organocopper species thus generated can be trapped by proton or ally! halide, affording tri- or tetrasubstituted allenes, respectively. The reaction, which is characterized by its mild reaction conditions and the utilization of cheap copper(1) iodide as catalyst, allows for synthesis of a variety of furan-substituted allenes with a wide range of functional groups tolerance. |
| URI | http://hdl.handle.net/20.500.11897/434483 |
| ISSN | 0022-3263 |
| DOI | 10.1021/acs.joc.6b00236 |
| Indexed | SCI(E) EI PubMed |
| Appears in Collections: | å å¦ä¸ å å å·¥ç¨ å¦é ¢ 生物有机与分子工程教育部重点实验室 |
