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DOI: 10.1055/sos-SD-043-00002

Hirsch, A.; Vostrowsky, O.Science of Synthesis, (20084342.

Monosubstituted acetylenes are successfully coupled by copper(II)-mediated oxidation in methanolic pyridine.[‌85‌] This technique, known as Eglinton coupling, is of great value for the syntheses of macrocyclic systems bearing a buta-1,3-diyne component (see also Section as, for example, in the cyclization of the terminally unsubstituted α,ω-alkadiyne 11 that gives cyclotetradeca-1,3-diyne (12) (Scheme 4).[‌86‌]

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Meeee M8 Meeeeeeeee Meeee (%) eee (°M) Mee
8 Me(MMe)8, eeeeeeee, 88°M 88 e.e. [‌8‌]
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8 Me(MMe)8M8M, MeMM/eeeeeeee (88:88) 88 888 (eee) [‌888‌]
8 Me(MMe)8M8M, MeMM/eeeeeeee (8:8) 88 >888 (eee) [‌888‌]
8 Me Me(MMe)8, Me8M/MeMM/eeeeeeee, eeeeee eeeee M8 ee M8 eeeee, ee 88 e.e. [‌888‌]
8 Me(MMe)8 (8.8 eeeee), eeeeeeee, eeeeee eeeee M8 ee M8 eeeee, ee 88 e.e. [‌888‌]

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