105-13-5Relevant articles and documents
Isochroman-3-ones ones via site-selective ring opening of benzocyclobutenones promoted by lithium tetramethylpiperidide and reaction with aromatic aldehydes
Matsumoto, Takashi,Hamura, Toshiyuki,Kuriyama, Yokusu,Suzuki, Keisuke
, p. 8985 - 8988 (1997)
In the presence of Li-TMP and an aromatic aldehyde, benzocyclobutenone undergoes an unusual heterolytic C(1)-C(4) bond fission, and subsequent reaction with the aldehyde gives, after acidic workup, isochroman-3-one in high yield.
CSJ acting as a versatile highly efficient greener resource for organic transformations
Maity, Himadri Sekhar,Misra, Kaushik,Mahata, Tanushree,Nag, Ahindra
, p. 24446 - 24450 (2016)
Simple, new, greener and efficient alternatives to the existing protocols have been developed for the reduction of aromatic aldehydes to their corresponding alcohols, decarboxylation of substituted benzoic acids (C6-C1) and substituted cinnamic acids (C6-C3) with a hydroxyl group at the para position with respect to the acid group to corresponding phenolic compounds and vinyl phenols respectively by using a natural feedstock, cucumber juice (CSJ), which acts as a greener solvent system, performing a substrate-selective reaction. Additionally, the hydrolysis of the acetyl as well as the benzoyl group of aromatic compounds has been carried out to afford excellent yield by CSJ.
Comparative study on reducing aromatic aldehydes by using ammonia borane and lithium amidoborane as reducing reagents
Xu, Weiliang,Fan, Hongjun,Wu, Guotao,Chen, Ping
, p. 1496 - 1501 (2012)
Lithium amidoborane (LiNH2BH3) and ammonia borane (NH3BH3) reduce aromatic aldehydes in tetrahydrofuran (THF) through two different pathways. LiNH2BH3 only transfers hydridic hydrogen on boron to aldehydes through a hydroboration process to achieve lithium aminoborate; ammonia borane, on the other hand, transfers both protic and hydridic hydrogens on N and B, respectively, to aldehydes to directly achieve corresponding alcohols. Mechanistic investigations confirm that protic H(N) and hydridic H(B) of ammonia borane participate in the reduction, in which the dissociation of both B-H and N-H bonds is likely to be involved in the rate-determining step. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012.
Water as a green solvent for fast and efficient reduction of carbonyl compounds with NaBH4 under microwave irradiation
Zeynizadeh, Behzad,Setamdideh, Davood
, p. 1179 - 1184 (2005)
Reduction of varieties of carbonyl compounds such as aldehydes, ketones, α,β-unsaturated aldehydes and ketones, α-diketones and acyloins was carried out very fast and efficiently by sodium borohydride in water under microwave irradiation. The corresponding product alcohols were obtained in high to excellent yields.
Homoleptic Zinc-Catalyzed Hydroboration of Aldehydes and Ketones in the Presence of HBpin
Kumar, Gobbilla Sai,Harinath, Adimulam,Narvariya, Rajrani,Panda, Tarun K.
, p. 467 - 474 (2020)
Here, we report the reaction between N-phenyl-o-phenylenediamine and pyrrole-2-carboxaldehyde to afford the N-phenyl-o-phenyl-enediiminopyrrole ligand {L-H2} in quantitative yield. A one-pot reaction between {L-H2} and diethylzinc (ZnEt2) in a 2:1 ratio afforded the homoleptic zinc metal complex [{L-H}2Zn] (1). The solid-state structures of ligand {L-H2} and zinc complex 1 were confirmed using X-ray crystallography. Further, complex 1 was used for chemoselective hydroboration of aldehydes and ketones in the presence of pinacolborane (HBpin) at ambient temperature to produce the corresponding boronate esters in high yield.
Potassium formate as a small molecule switch: Controlling oxidation-reduction behaviour in a two-step sequence
Willemsen, Jorgen S.,Van Hest, Jan C. M.,Rutjes, Floris P. J. T.
, p. 3143 - 3145 (2013)
A one-pot reaction sequence is described in which the addition of one compound allowed switching between simultaneously occurring oxidation and reduction reactions.
Arylboronic acid-facilitated selective reduction of aldehydes by tributyltin hydride
Yu,Wang
, p. 2719 - 2725 (2001)
Aldehydes were selectively reduced in the presence of a ketone with tributyltin hydride (n-Bu3SnH) and arylboronic acids. The double bond of an α-β-unsaturated system was not affected under the reaction conditions.
Modified hydroborate agent: (2,2′-bipyridyl)(tetrahydroborato)zinc complex, [Zn(BH4)2(bpy)], as a new, stable, efficient ligand-metal hydroborate and chemoselective reducing agent
Zeynizadeh, Behzad
, p. 317 - 326 (2003)
(2,2′-Bipyridyl)(tetrahydroborato)zinc complex, [Zn(BH4)2(bpy)], is a new white stable compound which has been used for efficient reduction of variety of carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α, β-unsaturated carbonyl compounds (1,2-reduction) to their corresponding alcohols in acetonitrile at room temperature. Excellent chemoselectivity was also observed for the reduction of aldehydes over ketones with this reducing agent.
High loading polymer reagents based on polycationic Ultraresins. Polymer-supported reductions and oxidations with increased efficiency
Barth, Michael,Shah, Syed Tasadaque Ali,Rademann, J?rg
, p. 8703 - 8709 (2004)
Ultraresin 1 was prepared from highly branched polyethylene imine (M n=10,000) via reductive cross-linking with terephthaldialdehyde. Following quaternization with methyl iodide, the polycationic Ultraresin 2, with iodide as a counterion, was obtained. These novel resins combine low swelling with high mechanical stability. By anion exchange polycationic Ultraresins carrying borohydride (3) and periodate (22) were generated and were investigated as very high loading polymer reagents. Ultra-borohydride resin 3 had a reducing activity of up to 12 mmol/g depending on the substrate. It proved successful in diverse reductions including those of aldehydes, ketones, and nitroolefines. The resin was employed in the reductive amination of aldehydes with an excess of amines, which were removed by the use of a scavenger resin. Periodate resin 22 was obtained with an active loading of up to 5.4 mmol/g and was employed in oxidations of sulfides, diols, hydroquinones, and hydrazines.
Highly efficient conversion of benzoates to alcohols with sodium borohydride in DME-MeOH
Zanka, Atsuhiko,Ohmori, Hiroki,Okamoto, Takumi
, p. 1636 - 1638 (1999)
Methoxybenzoates were quantitatively reduced to the corresponding alcohols with sodium borohydride in a mixed solvent (DME-MeOH). The described method was applicable to a large scale synthesis.
