Practical Methylenation Reaction for Aldehydes and Ketones Using New Julia-Type Reagents

Practical Methylenation Reaction for Aldehydes and Ketones Using New Julia-Type Reagents
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DOI:
10.1021/acs.orglett.5b01049
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发表时间:
2015-05-15
期刊:
影响因子:
5.2
通讯作者:
Uchida, Nariaki
Uchida, Nariaki
中科院分区:
化学1区
文献类型:
--
作者:
Ando, Kaori;Kobayashi, Takahisa;Uchida, Nariaki

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一种新的 Julia 型亚甲基化试剂 1-甲基-2-(甲基磺酰基)苯并咪唑 (1e) 在 NaHMLDS(-55 摄氏度至室温)或 t-BuOK(室温,1 小时)存在下在 DMF 中与各种醛和酮反应,以高产率生成相应的末端烯烃。副产物易于去除,反应条件温和实用。
A new Julia-type methylenation reagent, 1-methyl-2-(methylsulfonyl)benzimidazole (1e), reacts with a variety of aldehydes and ketones in the presence of either NaHMLDS (-55 degrees C to rt) or t-BuOK (rt, 1 h) in DMF to give the corresponding terminal alkenes in high yields. The byproducts are easily removed, and the reaction conditions are mild and practical.