Organic Chemistry Portal
Chemicals >> Reducing Agents

Ethanol


Recent Literature


The selective synthesis of Z-alkenes in alkyne semihydrogenation relies on the reactivity difference of the catalysts toward the starting materials and the products. In an Ir(III)-catalyzed semihydrogenation with EtOH as hydrogen source, an amine as additive is crucial to promote the alcoholysis. This catalytic system exhibits an unprecedented level of substrate scope, generality, and compatibility.
Z. Huang, Y. Wang, X. Leng, Z. Huang, J. Am. Chem. Soc., 2021, 143, 4809-4843.


A NCP-type pincer iridium complex enables an efficient, mild, chemoselective transfer hydrogenation of unactivated C-C multiple bonds with ethanol, forming ethyl acetate as the sole byproduct. A wide variety of alkenes, including multisubstituted alkyl alkenes, aryl alkenes, and heteroatom-substituted alkenes, as well as heteroarenes and internal alkynes, are suitable substrates.
Y. Wang, Z. Huang, X. Leng, H. Zhu, G. Liu, Z. Huang, J. Am. Chem. Soc., 2018, 140, 4417-4429.


A NCP-type pincer iridium complex enables an efficient, mild, chemoselective transfer hydrogenation of unactivated C-C multiple bonds with ethanol, forming ethyl acetate as the sole byproduct. A wide variety of alkenes, including multisubstituted alkyl alkenes, aryl alkenes, and heteroatom-substituted alkenes, as well as heteroarenes and internal alkynes, are suitable substrates.
Y. Wang, Z. Huang, X. Leng, H. Zhu, G. Liu, Z. Huang, J. Am. Chem. Soc., 2018, 140, 4417-4429.


A chiral (PCN)Ir complex catalyzes an asymmetric transfer hydrogenation of 1-aryl-1-alkylethenes with ethanol. The reaction offers high enantioselectivities, good functional group tolerance, and operational simplicity. A formal intramolecular asymmetric transfer hydrogenation of alkenols without an external H-donor, producing a tertiary stereocenter and remote ketone group simultaneously.
X. Tang, L. Qian, G. Liu, Z. Huang, Org. Lett., 2023, 25, 4950-4954.


Chiral iridium complexes ligated by anionic oxazoline-bearing NCP-type pincer ligands enable an asymmetric transfer hydrogenation (ATH) of diarylethenes using environmentally benign ethanol as the hydrogen donor. High enantioselectivities could be achieved for substrates bearing ortho-Me, ortho-Cl, or ortho-Br substituents on one of the aryl groups.
L. Qian, X. Tang, Z. Huang, Y. Wang, G. Liu, Z. Huang, Org. Lett., 2021, 23, 8978-8983.


The combination of a (PCN)Ir complex as the precatalyst and tBuNH2 as the cocatalyst mediates an efficient trans-semihydrogenation of 1,3-enynes with ethanol as the hydrogen source. The reaction provides an atom-economical access to unsymmetrical (E,E)-1,4-diarylbutadienes with high yields and stereoselectivities.
F. Huang, Z. Huang, G. Liu, Z. Huang, Org. Lett., 2022, 24, 5486-5490.


A bidentate Ru(II)-NC complex catalyzes a transfer hydrogenation of azoarenes to hydrazoarenes using ethanol as a hydrogen source in the presence of a weak base. Control experiments and density functional theory calculations suggest a Meerwein-Ponndorf-Verley mechanism with ethyl acetate as the byproduct.
D. Gong, D. Kong, N. Xu, Y. Hua, B. Liu, Z. Xu, Org. Lett., 2022, 24, 7339-7343.