Nickel-Catalyzed Suzuki-Miyaura Coupling of a Tertiary Iodocyclopropane with Wide Boronic Acid Substrate Scope: Coupling Reaction Outcome Depends on Radical Species Stability
Nickel-Catalyzed Suzuki-Miyaura Coupling of a Tertiary Iodocyclopropane with Wide Boronic Acid Substrate Scope: Coupling Reaction Outcome Depends on Radical Species Stability
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镍催化叔碘环丙烷与宽硼酸底物范围的 Suzuki-Miyaura 偶联：偶联反应结果取决于自由基物质稳定性
DOI：
10.1002/adsc.201401000
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发表时间：
2015
期刊：
影响因子：
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通讯作者：
Mitsuhiro Arisawa and Satoshi Shuto
中科院分区：
文献类型：
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作者：
Keisuke Yotsuji;Naoyuki Hoshiya;Takaaki Kobayashi;Hayato Fukuda;Hiroshi Abe;Mitsuhiro Arisawa and Satoshi Shuto
我们描述了镍催化的叔碘环丙烷与芳基硼酸的Suzuki-Miyaura芳基化;这是一种有效和收敛的策略，用于提供具有季立体中心的各种对映体富集的芳基环丙烷。这是叔烷基亲电试剂与各种芳族化合物（包括杂芳族化合物）之间的首次金属催化偶联。我们发现，与卤化物作为亲电试剂的Ni催化偶联的结果取决于反应期间形成的自由基物种的稳定性。使用叔丁醇（t-BuOH）作为反应溶剂是非常有效的，因为其在产生自由基的反应条件下的稳定性。
We describe a nickel‐catalyzed Suzuki–Miyaura arylation of a tertiary iodocyclopropane with arylboronic acids; this is an efficient and convergent strategy for providing various enantioenriched arylcyclopropanes with a quaternary stereogenic center. This is the first metal‐catalyzed coupling between a tertiary alkyl electrophile and a wide range of aromatics, including heteroaromatics. We found that the outcome of the Ni‐catalyzed coupling with halides as electrophiles was dependent on the stability of the radical species formed during the reaction. The use oftert‐butyl alcohol (t‐BuOH) as the reaction solvent was very effective, because of its stability under the radical‐generating reaction conditions.