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Silver salt-promoted direct cross-coupling reactions of alkynylsilanes with aryl iodides: synthesis of aryl-substituted alkynylamides

✍ Scribed by Yuji Koseki; Kunio Omino; Shinobu Anzai; Tatsuo Nagasaka

Book ID
104210052
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
116 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

A direct cross-coupling reaction of 5-trimethylsilyl-4-pentynamides (alkynylsilanes) 1 with aryl iodides, promoted by silver carbonate in the presence of palladium catalyst, afforded aryl-substituted alkynylamides 2, which readily underwent cyclization to form benzylidenelactams 3. This coupling reaction proved to be a useful for synthesis of aryl-substituted alkynes.

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The CuBr-promoted coupling reaction of [(dicthoxyphosphinyI)difluoromcthyI]~inc bromide 6 with aryl iodidcs in either DMF or DMA was cxamincd to give a series of aryl(difluoromcthyl)phosphonales. The coupling reaction was applicable to the sclcclive synthesis ol~a,a-difluoro+iodobcnzylphosphonale 1