Ethanol
Sandra Forbes
Product Manager
Recent Literature
The targeted synthesis of Z-alkenes during the semihydrogenation of alkynes hinges upon the distinct reactivity profiles exhibited by catalysts towards both the initial reactants and the resulting products. Within an Ir(III)-catalyzed semihydrogenation framework, utilizing EtOH as the hydrogen source, the inclusion of an amine additive plays a pivotal role in facilitating the alcoholysis process. This tailored catalytic system showcases an unparalleled degree of versatility, accommodating a wide array of substrates, as well as remarkable compatibility, marking a significant advancement in the field.
Z. Huang, Y. Wang, X. Leng, Z. Huang, J. Am. Chem. Soc., 2021, 143, 4809-4843.
DOI: 10.1021/jacs.1c01472
The utilization of an NCP-type pincer iridium complex facilitates an efficient, gentle, and chemoselective transfer hydrogenation process of unreactive C-C multiple bonds, employing ethanol as the hydrogen source, with ethyl acetate being the sole byproduct. This methodology demonstrates compatibility with a broad spectrum of alkenes, encompassing multisubstituted alkyl alkenes, aryl alkenes, heteroatom-substituted alkenes, along with heteroarenes and internal alkynes, all serving as viable substrates.
Y. Wang, Z. Huang, X. Leng, H. Zhu, G. Liu, Z. Huang, J. Am. Chem. Soc., 2018, 140, 4417-4429.
DOI: 10.1021/jacs.8b01038
An NCP-based pincer iridium complex effectively catalyzes the transfer hydrogenation of unactivated C-C multiple bonds using ethanol under mild and chemoselective conditions, resulting in the exclusive formation of ethyl acetate as a byproduct. This system exhibits a remarkable substrate scope, accommodating a diverse range of alkenes such as multisubstituted alkyl alkenes, aryl alkenes, heteroatom-substituted alkenes, as well as heteroarenes and internal alkynes.
Y. Wang, Z. Huang, X. Leng, H. Zhu, G. Liu, Z. Huang, J. Am. Chem. Soc., 2018, 140, 4417-4429.
DOI: 10.1021/jacs.8b01038
A chiral (PCN)Ir complex proficiently catalyzes the asymmetric transfer hydrogenation of 1-aryl-1-alkylethenes employing ethanol as the hydrogen source. This reaction boasts high enantioselectivities, impressive functional group compatibility, and operational ease. Additionally, it enables a formal intramolecular asymmetric transfer hydrogenation of alkenols without the need for an external H-donor, thereby simultaneously affording a tertiary stereocenter and a remote ketone group.
X. Tang, L. Qian, G. Liu, Z. Huang, Org. Lett., 2023, 25, 4950-4954.
DOI: 10.1021/acs.orglett.3c01880
Chiral iridium complexes, featuring anionic oxazoline-containing NCP-type pincer ligands, facilitate an asymmetric transfer hydrogenation (ATH) of diarylethenes, harnessing environmentally friendly ethanol as the hydrogen donor. These catalysts demonstrate remarkable enantioselectivity for substrates adorned with ortho-Me, ortho-Cl, or ortho-Br substituents on one of the aryl rings.
L. Qian, X. Tang, Z. Huang, Y. Wang, G. Liu, Z. Huang, Org. Lett., 2021, 23, 8978-8983.
DOI: 10.1021/acs.orglett.1c03455
A synergistic partnership between a (PCN)Ir complex, serving as the precatalyst, and tBuNH2, functioning as the cocatalyst, facilitates an efficient trans-semihydrogenation of 1,3-enynes, utilizing ethanol as the hydrogen source. This reaction offers an atom-economical route to producing unsymmetrical (E,E)-1,4-diarylbutadienes with high yields and impressive stereoselectivities.
F. Huang, Z. Huang, G. Liu, Z. Huang, Org. Lett., 2022, 24, 5486-5490.
DOI: 10.1021/acs.orglett.2c02327
The nickel-catalyzed asymmetric transfer hydrogenation of α,β-unsaturated ketimines, employing environmentally benign ethanol as the hydrogen donor, enables the synthesis of chiral allylic amines under mild conditions. This catalytic system further demonstrates its proficiency in selectively synthesizing C1-deuterated chiral allylic amines in high yields, utilizing solely stoichiometric amounts of 2-propanol-d8 as the deuterium source.
L. Zhang, Y. Zhu, P. Li, P. Yang, B. Tang, Org. Lett., 2023, 25, 8739-8744.
DOI: 10.1021/acs.orglett.3c03650
A bidentate Ru(II)-NC complex effectively catalyzes the transfer hydrogenation of azoarenes to hydrazoarenes, employing ethanol as the hydrogen source in the presence of a weak base. Mechanistic insights gained from control experiments and supported by density functional theory calculations point towards a Meerwein-Ponndorf-Verley pathway, with ethyl acetate emerging as the sole byproduct of the reaction.
D. Gong, D. Kong, N. Xu, Y. Hua, B. Liu, Z. Xu, Org. Lett., 2022, 24, 7339-7343.
DOI: 10.1021/acs.orglett.2c02866
Quoted from: https://www.organic-chemistry.org/chemicals/reductions/ethanol.shtm
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