Abstract
We report an iron(III)-catalyzed intermolecular C(sp² )-C(sp³ )
dehydration coupling reaction between ketene dithioacetals and propargyl
alcohols, leading to the synthesis of gem -dialkylthiopenten-4-ynes
in high efficiency. The products could be transformed into methyl
pent-4-ynoates in high yields.
Key words
iron - dehydration - coupling reactions - alkynes - thioacetals
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8 Synthesis of gem -dialkylthiopenten-4-ynes
(3 ); Typical procedure with 3a :
To a solution of 1-(1,3-dithiolan-2-ylidene)propan-2-one (1a ; 160 mg, 1.0 mmol) and 1,3-diphenylprop-2-yn-1-ol
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as a white solid. Mp 170-171 ˚C. ¹ H
NMR (CDCl3 , 500 Hz): δ = 2.17 (s, 3 H),
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NMR (CDCl3 , 125 Hz): δ = 28.4, 35.9,
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128.6, 131.6, 138.5, 163.8, 194.7. HRMS (ESI-TOF): m /z [M + H]+ calcd
for C21 H19 OS2 : 351.0877; found:
351.0833
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