Expedient Iron-Catalyzed Coupling of Alkyl, Benzyl and Allyl Halides with Arylboronic Esters
Expedient Iron-Catalyzed Coupling of Alkyl, Benzyl and Allyl Halides with Arylboronic Esters
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DOI：
10.1002/chem.201402174
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发表时间：
2014-06-23
影响因子：
4.3
通讯作者：
Pye, Dominic R.
中科院分区：
文献类型：
--
作者：
Bedford, Robin B.;Brenner, Peter B.;Pye, Dominic R.
虽然很有吸引力，但铁催化的芳基硼试剂与烷基卤化物的偶联通常需要昂贵的或具有合成挑战性的双膦配体。在这里，我们证明了伯烷基溴和仲烷基溴和氯化物，以及苯基和烯丙基卤化物，可以用非常简单的铁基催化剂与烷基锂试剂活化的芳基硼酸酯偶联。所使用的催化剂要么是廉价且广泛使用的双膦加合物，要么在许多情况下是简单的[Fe(Acac)(3)]，没有添加共配体。在前一种情况下，初步的机理研究强调了铁(I)-膦中间体的可能参与。
While attractive, the iron-catalyzed coupling of arylboron reagents with alkyl halides typically requires expensive or synthetically challenging diphosphine ligands. Herein, we show that primary and secondary alkyl bromides and chlorides, as well as benzyl and allyl halides, can be coupled with arylboronic esters, activated with alkyllithium reagents, by using very simple iron-based catalysts. The catalysts used were either adducts of inexpensive and widely available diphosphines or, in a large number of cases, simply [Fe(acac)(3)] with no added co-ligands. In the former case, preliminary mechanistic studies highlight the likely involvement of iron(I)-phosphine intermediates.