Towards Iron-Catalysed Suzuki Biaryl Cross-Coupling: Unusual Reactivity of 2-Halobenzyl Halides
Towards Iron-Catalysed Suzuki Biaryl Cross-Coupling: Unusual Reactivity of 2-Halobenzyl Halides
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DOI：
10.1055/s-0034-1380135
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发表时间：
2015-02
期刊：
影响因子：
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通讯作者：
R. Bedford;T. Gallagher;Dominic R. Pye;W. Savage
中科院分区：
文献类型：
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作者：
R. Bedford;T. Gallagher;Dominic R. Pye;W. Savage
摘要2-卤代苄基卤与硼酸根阴离子Li [（Ph）（t-Bu）Bpin]的反应不仅导致预期的苄基位置的芳基化，而且还导致一些Suzuki联芳基交叉偶联。初步的机理研究暗示了苄基铁中间体的中间性，其可以：（a）与芳基硼试剂直接交叉偶联以给出观察到的单芳基化物质，或（B）在与硼基亲核试剂反应时经历芳基卤化物的氧化加成以产生二芳基化物质。
Abstract The reaction of 2-halobenzyl halides with the borate anion Li[(Ph)(t-Bu)Bpin] leads not only to the expected arylation at the benzyl position, but also to some Suzuki biaryl cross-coupling. Preliminary mechanistic investigations hint towards the intermediacy of benzyl iron intermediates that can either: (a) directly cross-couple with the aryl boron reagent to give observed monoarylated species, or (b) undergo oxidative addition of the aryl halide to generate the diarylated species on reaction with the boron-based nucleophile.