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A green and sustainable electrochemical hydroboration of carbonyl compounds with HBpin has been reported for the first time. Under catalyst-free and additive-free mild reaction conditions the corresponding boronic esters were obtained in excellent yields via the simple electrochemical hydroboration of various aldehydes and ketones with HBpin at room temperature. The scale-up reaction demonstrated potential practical applications. A plausible reaction mechanism was proposed based on the corresponding deuterium-labelling, radical inhibition and cyclic voltammetry experiments.

A palladium-catalyzed deuterated formylation of aryl sulfonium salts is prepared conveniently from readily available arenes, which enables the expedient synthesis of a series of structurally diverse C-1 deuterated aldehydes with 96%-99% deuterium incorporation. The easy to handle and cost-effective DCOONa provides a deuterium source, which can be introduced onto the formyl units with excellent selectivity under the palladium-catalytic redox neutral conditions. This catalytic route can accomplish the direct late-stage C-H functionalization of bioactive molecules and natural product derivatives assisted by C (sp 2 )-H thianthrenation. Moreover, on the basis of this practical approach, several deuterated drugs and analogues could be prepared with excellent levels of deuterium incorporation.

A green and sustainable electrochemical hydroboration of carbonyl compounds with HBpin has been reported for the first time. Under catalyst-free and additive-free mild reaction conditions the corresponding boronic esters were obtained in excellent yields via the simple electrochemical hydroboration of various aldehydes and ketones with HBpin at room temperature. The scale-up reaction demonstrated potential practical applications. A plausible reaction mechanism was proposed based on the corresponding deuterium-labelling, radical inhibition and cyclic voltammetry experiments. [ABSTRACT FROM AUTHOR]

Abstract A NCN-pincer ligand-based Mg-Li bimetallic complex [NCN-MgBr 2 ][Li(THF) 4 ] 1 has been employed as an efficient catalyst for cyanosilylation of a wide range of aldehydes with trimethylsilyl cyanide (TMSCN) at room temperature in CDCl 3. In addition, catalyst 1 shows a good tolerance towards various functional groups such as amide, acid, ester, heterocyclic and alkene etc. The chemoselective cyanosilylation of aldehydes over ketones was also achieved under these conditions. Graphical abstract Image 1 Highlights • A Mg-Li bimetallic complex has been employed as an efficient catalyst for various aldehyde cyanosilylation. • The catalyst 1 shows a high tolerance towards various functional groups such as amide, acid, ester etc. • Chemoselective cyanosilylation of aldehydes over ketones was observed. [ABSTRACT FROM AUTHOR]

The well-defined lithium NCN-Pincer magnesiate complex [Li (THF) 4 ][NCN-MgBr 2 ] 2 based on a bis(imino)aryl ligand has been successfully prepared, crystallographic characterized and employed as an efficient catalyst for hydroboration of a wide range of aldehydes and ketones with pinacolborane (HBpin) at room temperature. Both aldehyde and ketone hydroboration proceeded efficiently (>99% conversion in <15 min) and could be directly carried out in a CDCl 3 solution. In addition, chemoselective hydroboration of aldehydes over ketones was also achieved under these conditions. [ABSTRACT FROM AUTHOR]

Simple, commercially available Grignard reagents have been used as highly efficient precatalysts for the hydroboration of a wide range of aldehydes and ketones. The reaction employs very low catalyst loadings (aldehydes: 0.05 mol%, ketones: 0.5 mol%), and proceeds rapidly (aldehydes: 10 min, ketones: 20 min) under neat condition at room temperature. The Grignard reagent catalyst demonstrated good substrate scope, functional group tolerance, and high chemoselectivity in the carbonyl hydroboration. DFT calculations were performed to investigate the possible reaction mechanism. In contrast to the traditional stoichiometric use of Grignard reagents, this newly developed protocol provides a catalytic application of these reagents for molecular transformations. Image 1 • Grignard reagents have been employed as efficient precatalysts for various carbonyl hydroboration. • The Grignard reagent catalyst shows a high functional group tolerance and high chemoselectivity. • In contrast to the traditional stoichiometric use of Grignard reagents, this protocol provides a catalytic application. [ABSTRACT FROM AUTHOR]