728-80-3Relevant articles and documents
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.
Grignard Reagents on a Tab: Direct Magnesium Insertion under Flow Conditions
Huck, Lena,De La Hoz, Antonio,Díaz-Ortiz, Angel,Alcázar, Jesus
supporting information, p. 3747 - 3750 (2017/07/26)
An on-demand preparation of organomagnesium reagents is presented using a new flow protocol. The risks associated with the activation of magnesium are circumvented by a new on-column initiation procedure. Required amounts of solutions with a precise titration were obtained. Telescoped flow or batch reactions allow access to a diverse set of functional groups.
Nonracemic diarylmethanols from CuH-catalyzed hydrosilylation of diaryl ketones
Lee, Ching-Tien,Lipshutz, Bruce H.
supporting information; experimental part, p. 4187 - 4190 (2009/05/30)
(Chemical Equation Presented) An efficient method for the synthesis of nonracemic diarylmethanols has been developed. The use of (R)-(-)-(DTBM-SEGPHOS) CuH effects highly enantioselective 1,2-hydrosilylation of prochiral diaryl ketones.