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Corey–Fuchs Alkyne Synthesis
A Synthetic Method for Formyl → Ethynyl Conversion (RCHO → RC≡CH or RC≡CR′).
Tetrahedron Lett. 1972;
In 1972, Corey and Fuchs reported a convenient transformation of aldehydes to the corresponding one-carbon chain-extended alkynes using carbon tetrabromide and triphenylphosphine and subsequently n-BuLi. The method provides the desired alkynes in good yields.
The procedure comprises two steps. The synthesis of the dibromoolefin can be conducted in two ways in a Wittig-type reaction. In the second step, treatment of the prepared dibromoolefins with two equivalents n-BuLi furnishes the desired terminal alkynes. Remarkably, the intermediate lithium acetylide can also be treated with a variety of electrophiles.
17 September 2020 (online)
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