化学
试剂
废止
烷基
组合化学
过渡金属
催化作用
有机合成
偶联反应
有机化学
计算化学
激进的
光化学
作者
Lei Liu,Maria Camila Aguilera,Wes Lee,Cassandra R. Youshaw,Michael L. Neidig,Osvaldo Gutiérrez
出处
期刊:Science
[American Association for the Advancement of Science (AAAS)]
日期:2021-10-22
卷期号:374 (6566): 432-439
被引量:44
标识
DOI:10.1126/science.abj6005
摘要
Transition metal–catalyzed cross-coupling reactions are some of the most widely used methods in chemical synthesis. However, despite notable advantages of iron (Fe) as a potentially cheaper, more abundant, and less toxic transition metal catalyst, its practical application in multicomponent cross-couplings remains largely unsuccessful. We demonstrate 1,2-bis(dicyclohexylphosphino)ethane Fe–catalyzed coupling of α-boryl radicals (generated from selective radical addition to vinyl boronates) with Grignard reagents. Then, we extended the scope of these radical cascades by developing a general and broadly applicable Fe-catalyzed multicomponent annulation–cross-coupling protocol that engages a wide range of π-systems and permits the practical synthesis of cyclic fluorous compounds. Mechanistic studies are consistent with a bisarylated Fe(II) species being responsible for alkyl radical generation to initiate catalysis, while carbon-carbon bond formation proceeds between a monoarylated Fe(II) center and a transient alkyl radical.
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