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Synfacts 2020; 16(10): 1199
DOI: 10.1055/s-0040-1706429
Metals in Synthesis

Corey–Fuchs Alkyne Synthesis

Contributor(s):
Paul Knochel
,
Andreas Hess
Corey EJ, *, Fuchs PL. Harvard University, Cambridge, USA
A Synthetic Method for Formyl → Ethynyl Conversion (RCHO → RC≡CH or RC≡CR′).

Tetrahedron Lett. 1972;
13: 3769-3772
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Key words

aldehydes - terminal alkynes - dibromoolefins

Significance

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.


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Comment

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.


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Publication History

Article published online:
17 September 2020

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