Direct Preparation of 3-Thienyl Organometallic Reagents: 3-Thienylzinc and 3-Thienylmagnesium Iodides and 3-Thienylmanganese Bromides and Their Coupling Reactions
1997; American Chemical Society; Volume: 62; Issue: 20 Linguagem: Inglês
10.1021/jo970778b
ISSN1520-6904
AutoresReuben D. Rieke, Seung‐Hoi Kim, Xiaoming Wu,
Tópico(s)Synthesis and Reactivity of Sulfur-Containing Compounds
Resumo3-Thienylzinc and 3-thienylmagnesium iodides can be generated from the direct oxidative addition of Rieke zinc and magnesium to 3-iodothiophene, respectively. The direct preparation of 3-thienylmanganese bromides from the reaction of Rieke manganese with 3-bromothiophene and 3,4-dibromothiophene is also performed. These 3-thienyl organometallic reagents have been found to be regiostable intermediates and undergo coupling reactions with a variety of versatile electrophiles such as acid chlorides, aryl iodides, aldehydes, and disulfide.
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