Synthesis of ferrocenyl alkenes, dienes, and enynes via samarium diiodide promoted tandem addition and dehydration of ferrocenyl carbonyls with halides.
A practical method for preparation of ferrocenyl alkenes, dienes, and enynes from ferrocenyl carbonyls was explored. A one-pot operation using samarium diiodide to promote the condensation reactions of ferrocenecarboxaldehyde, acetylferrocene, benzoylferrocene, and butanoylferrocene with benzyl bromides, allyl bromide, propargyl bromide, and 1-bromo-3-chlorobutane gave the olefinic products in very high yields. The condensation reactions were also achieved by using catalytic amounts of SmI(2) with magnesium to regenerate the divalent samarium reducing agent.
Jong
S J
SJ
Department of Chemistry, National Taiwan University, Taipei, Taiwan 106, Republic of China.
Fang
J M
JM