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31.2.3.2.1.3 Synthesis of Arylalkynes

DOI: 10.1055/sos-SD-131-00075

Stanforth, S. P.Science of Synthesis Knowledge Updates, (20151197.

The Sonogashira reaction between chloroarenes 51 and alkynes 52 usually affords arylalkynes 53 in good yield and some representative examples are collected in Scheme 26. These reactions illustrate the range of catalysts, ligands, and other conditions (e.g., conventional heating or microwave) that have been employed. Sterically encumbered chlo­roarenes (e.g., 2,6-dimethylchlorobenzene; 51, Ar1 = 2,6-Me2C6H3) can also be utilized in the Sonogashira reaction.[‌78‌‌80‌] When the alkyne is a 2-methylbut-3-yn-2-ol derivative 52 (X = CMe2OH), a deacetonative cross-coupling reaction takes place,[‌81‌] and with propynoic acid derivatives 52 (X = CO2H), decarboxylative cross-coupling reactions occur.[‌82‌] Heterogeneous catalysts have also been developed for application in the Sonogashira reaction.[‌23‌] 2-Chlorophenol and related compounds participate in the Sonogashira reaction, but the arylalkynes that are formed are not isolated but subsequently undergo an intramolecular cyclization at the phenolic moiety, affording benzofurans as products.[‌83‌]

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Meeeeeeeeee 88

Me8 M8 M Meeeeeeeeee Meeee (%) Mee
Me Me M Me/M (88% e/e; 8 eee%), MMeee (8 eee%), M8MM8, MMM, 888 °M, 8 e 88 [‌88‌]
Me (MM8)8Me M MeMe8(MMe8)8 (8 eee%), e-Me8M (8 eee%), MMM, Me8MM8, MMM, eeeeeeeee, 888 °M, 88 eee 88 [‌88‌]
8-Mee Me M 88 (8 eee%), MMeee (8 eee%), MMMM, eeeeeeeeeee, M8M, eeeeeeeee, 888 °M, 88 eee 88 [‌88‌]
8-Mee Me M MeMe8(MMe8)8 (8 eee%), e-Me8M (8 eee%), MMM, Me8MM8, MMM, eeeeeeeee, 888 °M, 88 eee 88 [‌88‌]
8,8-Me8M8M8 Me M 88 (8 eee%), MMeee (8 eee%), MMMM, eeeeeeeeeee, M8M, eeeeeeeee, 888 °M, 88 eee 88 [‌88‌]
8,8-Me8M8M8 Me M Me/M (88% e/e; 8 eee%), MMeee (8 eee%), M8MM8, MMM, 888 °M, 8 e 88 [‌88‌]
8,8-Me8M8M8 Me M MeMe8(MMe8)8 (8 eee%), e-Me8M (8 eee%), MMM, Me8MM8, MMM, eeeeeeeee, 888 °M, 88 eee 88 [‌88‌]
8-M8MM8M8 Me M Me/M (88% e/e; 8 eee%), MMeee (8 eee%), M8MM8, MMM, 888 °M, 8 e 88 [‌88‌]
8-MeM8MM8M8 (MM8)8Me M MeMe8(MMMe)8 (8 eee%), 88 (8 eee%), Me8MM8, eeeeeee, 88 °M, 88 e 88 [‌88‌]
8-MeM8MM8M8 MMM M MeMe8(MMMe)8 (8 eee%), 88 (8 eee%), Me8MM8, eeeeeee, 88 °M, 88 e 88 [‌88‌]
Me Me MMe8MM 88 (8 eee%), MMeee (8 eee%), M8MM8, MeMM, 888 °M, 88 e 88 [‌88‌]
8-M8MM8M8 Me MMe8MM 88 (8 eee%), MMeee (8 eee%), M8MM8, MeMM, 888 °M, 88 e 88 [‌88‌]
8-Mee Me MM8M 88 (8 eee%), MMeee (8 eee%), M8MM8, eeeeee/M8M, 888 °M, 8 e 88 [‌88‌]
8-M8MM8M8 Me MM8M 88 (8 eee%), MMeee (8 eee%), M8MM8, eeeeee/M8M, 888 °M, 8 e 88 [‌88‌]
8-M8MM8M8 (MM8)8Me MM8M 88 (8 eee%), MMeee (8 eee%), M8MM8, eeeeee/M8M, 888 °M, 8 e 88 [‌88‌]

e MMeee = 8-(eeeeeeeeeeeeeeeeeeeee)-8′,8′,8′-eeeeeeeeeeeeeeeeeeee; MMMM = eeeeee eeeeeeeeeeeeeeeeeeeeeee.

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeeeee (88, Me8 = M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

MeMe (8.888 e, 8.8 eeee), 8-eeeeee-8-eeeeeeeee-8-ee-8-ee (8.88 e, 8.8 eeee), M8MM8 (8.888 e, 8.8 eeee), eeeeeeee 88 (8 eee%), eee MMeee (8.8 ee, 8.888 eeee) eeee eeeeeeeee ee MeMM (8 eM) ee e 88-eM eeee eeeee e M8 eeeeeeeeee. Mee eeeeeee eee eeeeee ee 888 °M (eee eeee eeeeeeeeeee) eee 88 e. Mee eeeeeee eee eeeeeee ee eeee ee ee eee eee eeeeeeee eeeeeee e eee ee Meeeee. Meeee eee eeeee ee eee eeeeeeee eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 ×). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe), eeeeee eee eeeeeee ee e eeeee eeeee; eeeee: 88 ee (88%); ee 88–88 °M.

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