A facile, general method for the preparation of fluorinated enynes

✍ Scribed by Yang Zhen-Yu; Donald J Burton

• Book ID: 104222076
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 216 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)88808-5

✦ Synopsis

Fluorinated vinyl iodide% RlCF=CFI [where Rl=F, CFs, Ph, (iPrC)sP(O)], couple directly with 1-alkynes in the presence of palladium and cuprous iodide in triethylamine to give excellent yields of the fluorinated enynes.

Recent reports have demonstrated the importance of enynes in organic synthesis.

Conjugated enynes react selectively with electrophiles at the double bond to provide an efficient method for the assembly of multifunctional molecules1 and they have been utilized as essential components in the synthesis of natural products 2. Thus, one would anticipate that fluorinecontaining enynes would also be useful as building blocks to partially fluorinated multifunctional molecules or partially fluorinated natural products. However, the lack of general synthetic methodology for the preparation of fluorinated enynes has hampered development along these lines. In this communication we wish to describe a facile, direct, and practical method for the general preparation of this class of compounds.