35060-38-9Relevant articles and documents
Electrochemically driven catalytic Pd(0)/Cr(II) mediated coupling of organic halides with aldehydes. The Nozaki-Hiyama-Kishi reaction
Grigg, Ronald,Putnikovic, Bogdan,Urch, Christopher J.
, p. 6307 - 6308 (1997)
An electrochemically driven, catalytic, Pd(0)/Cr(II) mediated coupling of organic halides with aldehydes is described. The reaction proceeds under mild conditions and the influence of reaction conditions and the mechanism are briefly discussed.
Catalytic Aldehyde and Alcohol Arylation Reactions Facilitated by a 1,5-Diaza-3,7-diphosphacyclooctane Ligand
Isbrandt, Eric S.,Nasim, Amrah,Newman, Stephen G.,Zhao, Karen
supporting information, p. 14646 - 14656 (2021/09/18)
We report a catalytic method to access secondary alcohols by the coupling of aryl iodides. Either aldehydes or alcohols can be used as reaction partners, making the transformation reductive or redox-neutral, respectively. The reaction is mediated by a Ni catalyst and a 1,5-diaza-3,7-diphosphacyclooctane. This P2N2ligand, which has previously been unrecognized in cross-coupling and related reactions, was found to avoid deleterious aryl halide reduction pathways that dominate with more traditional phosphines and NHCs. An interrupted carbonyl-Heck type mechanism is proposed to be operative, with a key 1,2-insertion step forging the new C-C bond and forming a nickel alkoxide that may be turned over by an alcohol reductant. The same catalyst was also found to enable synthesis of ketone products from either aldehydes or alcohols, demonstrating control over the oxidation state of both the starting materials and products.
Bulky N-Heterocyclic-Carbene-Coordinated Palladium Catalysts for 1,2-Addition of Arylboron Compounds to Carbonyl Compounds
Okuda, Yuta,Nagaoka, Masahiro,Yamamoto, Tetsuya
, p. 6291 - 6300 (2020/11/30)
The synthesis of primary, secondary, and tertiary alcohols by the 1,2-addition of arylboronic acids or boronates to carbonyl compounds, including unactivated ketones, using novel bulky yet flexible N-heterocyclic carbene (NHC)-coordinated 2,6-di(pentan-3-yl)aniline (IPent)-based cyclometallated palladium complexes (CYPs) as catalysts is reported. The PhS-IPent-CYP-catalyzed reactions are efficient at low catalyst loadings (0.02–0.3 mol% Pd), and the exceptional catalytic activity for 1,2-addition is attributed to the steric bulk of the NHC ligand. These reactions can yield a wide range of functionalized benzylic alcohols that are difficult to synthesize by classical protocols using highly active organomagnesium or lithium reagents.