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Search for "Glaser–Hay reaction" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.
Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp3)–H to construct C–C bonds
- Hui Yu and
- Feng Xu
Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94
- significantly different reactivity and chemical selectivity from noble metals (Ru, Rh, Pd). Compared with noble metals, copper catalysts are cheaper and easier to obtain, making Cu more advantageous for industrial applications of C–H functionalization reactions. The Glaser–Hay reaction may be one of the oldest
Graphical Abstract
Scheme 1: Research progress of coupling reactions and active compounds containing α-C(sp3)-functionalized eth...
Scheme 2: Transition-metal-catalyzed CDC pathways.
Scheme 3: CDC of active methylene compounds in the α-C(sp3) position of ethers.
Scheme 4: InCl3/Cu(OTf)2/NHPI co-catalyzed CDC reaction.
Scheme 5: CDC of cyclic benzyl ethers with aldehydes.
Scheme 6: Cu-catalyzed CDC of (a) unactivated C(sp3)–H ethers with simple ketones and (b) double C(sp3)−H fun...
Scheme 7: Cu-catalyzed CDC of C(sp3)–H/C(sp3)–H bonds.
Scheme 8: Cu-catalyzed synthesis of chiral 2-substituted tetrahydropyrans.
Scheme 9: CDC of thiazole with cyclic ethers.
Scheme 10: Cu(I)-catalyzed oxidative alkenylation of simple ethers.
Scheme 11: Cross-dehydrogenation coupling of isochroman C(sp3)–H bonds with anisole C(sp2)–H bonds.
Scheme 12: Pd(OAc)2/Cu(OTf)2-catalyzed arylation of α-C(sp3)–H bonds of ethers.
Scheme 13: Cu-catalyzed C(sp3)–H/C(sp2)–H activation strategies to construct C(sp3)–C(sp2) bonds.
Scheme 14: Cu(I)-catalyzed C(sp2)–H alkylation.
Scheme 15: Cu-catalyzed C(sp3)–H/C(sp)–H activation to construct C(sp3)–C(sp) bonds (H2BIP: 2,6-bis(benzimidaz...
Scheme 16: Fe-catalyzed CDC reaction pathways.
Scheme 17: Fe2(CO)9-catalyzed functionalization of C–H bonds.
Scheme 18: Ligand-promoted Fe-catalyzed CDC reaction of N-methylaniline with ethers.
Scheme 19: Fe-catalyzed CDC of C(sp3)–H/C(sp3)–H bonds.
Scheme 20: Fe-catalyzed hydroalkylation of α,β-unsaturated ketones with ethers.
Scheme 21: Solvent-free Fe(NO3)3-catalyzed CDC of C(sp3)–H/C(sp2)–H bonds.
Scheme 22: Alkylation of disulfide compounds to afford tetrasubstituted alkenes.
Scheme 23: Fe-catalyzed formation of 1,1-bis-indolylmethane derivatives.
Scheme 24: Alkylation of coumarins and flavonoids.
Scheme 25: Direct CDC α-arylation of azoles with ethers.
Scheme 26: CDC of terminal alkynes with C(sp3)–H bonds adjacent to oxygen, sulfur or nitrogen atoms.
Scheme 27: Alkylation of terminal alkynes.
Scheme 28: Co-catalyzed functionalization of glycine esters.
Scheme 29: Co-catalyzed construction of C(sp2)–C(sp3) bonds.
Scheme 30: Co-catalyzed CDC of imidazo[1,2-a]pyridines with isochroman.
Scheme 31: Co-catalyzed C–H alkylation of (benz)oxazoles with ethers.
Scheme 32: Cobalt-catalyzed CDC between unactivated C(sp2)–H and C(sp3)–H bonds.
Scheme 33: MnO2-catalyzed CDC of the inactive C(sp3)-H.
Scheme 34: Oxidative cross-coupling of ethers with enamides.
Scheme 35: Ni(II)-catalyzed CDC of indoles with 1,4-dioxane.
Scheme 36: Chemo- and regioselective ortho- or para-alkylation of pyridines.
Scheme 37: Asymmetric CDC of 3,6-dihydro-2H-pyrans with aldehydes.
Scheme 38: CDC of heterocyclic aromatics with ethers.
Scheme 39: Indium-catalyzed alkylation of DHPs with 1,3-dicarbonyl compounds.
Scheme 40: Rare earth-metal-catalyzed CDC reaction.
Scheme 41: Visible-light-driven CDC of cycloalkanes with benzazoles.
Scheme 42: Photoinduced alkylation of quinoline with cyclic ethers.
Scheme 43: Photocatalyzed CDC reactions between α-C(sp3)–H bonds of ethers and C(sp2)–H bonds of aromatics.
Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene
- Semyon V. Tsybulin,
- Ekaterina A. Filatova,
- Alexander F. Pozharskii,
- Valery A. Ozeryanskii and
- Anna V. Gulevskaya
Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49
- systems; 1,4-diaryl-1,3-butadiynes; donor–acceptor systems; Glaser–Hay reaction; Introduction π-Conjugated oligomers and polymers attracted considerable attention from the very start as a promising class of semiconductors, chemosensors, and various electronic devices [1][2]. Although silicon and
Graphical Abstract
Figure 1: Proton sponge-based 1,4-diaryl-1,3-butadiynes synthesized previously and in this study.
Figure 2: Target oligomers as push–pull and cross-conjugated π-systems.
Scheme 1: Synthetic strategy for target oligomers 5.
Scheme 2: Synthesis of 7-(arylethynyl)-2-ethynyl-DMAN 6.
Scheme 3: Synthesis of 1,4-diaryl-1,3-butadiynes 5 and their salts 11.
Figure 3: Molecular structures of compounds 5b (top), 5d (middle), and 5e (bottom).
Figure 4: Views on the molecular backbone of compounds 5b (top), 5d (middle), and 5e (bottom) along the napht...
Scheme 4: Transformation of butadiyne 5c into benzo[g]indole 12.
Figure 5: Molecular structure of compound 11c: frontal (top; BF4− omitted) and side views (bottom; hydrogen a...
Figure 6: Calculation of the qr parameter.
Figure 7: Two π-conjugation ways in oligomers 5.
Figure 8: UV–vis spectra of oligomers 5 (blue line), monomers 6 (red line), and butadiyne 1 (green line).
Figure 9: UV–vis spectra of salts 11 (left), 1·2HBF4 and 6b·HBF4 (right) in acetonitrile.
Figure 10: π-Conjugation pathway in salts 11b and 6b·HBF4.
Figure 11: Cyclic voltammograms of oligomers 5.
Scheme 5: Possible ways of one- and two-electron oxidation of oligomers 5.
