Electrochemically Driven Deoxygenative Borylation of Alcohols and Carbonyl Compounds.

We present a new, unified approach for the transformation of benzylic and allylic alcohols, aldehydes, and ketones into boronic esters under electroreductive conditions. Key to our strategy is the use of readily available pinacolborane, which serves both as an activator and an electrophile by first generating a redox-active trialkylborate species and then delivering the desired deoxygenatively borylated product. This strategy is applicable to a variety of substrates and can be employed for the late-stage functionalization of complex molecules.

Titanium Radical Redox Catalysis: Recent Innovations in Catalysts, Reactions, and Modes of Activation.

Radical chemistry has emerged as a cornerstone in modern organic synthesis, providing chemists with numerous new tools to rapidly expand reactivity and chemical space in academic and industrial research. In this regard, titanium complexes have been recognized as an attractive class of catalysts owing to their rich redox activities in addition to the abundance and low toxicity of this early transition metal. Traditionally employed for the activation of epoxides and carbonyl compounds, Ti radical redox catalysis has broken into new grounds in recent years, giving rise to a diverse repertoire of useful transformations.

Enantioselective Synthesis of -Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(CF) and a Chiral Lewis Acid Co-Catalyst.

We disclose a catalytic method for β-C(sp)-H functionalization of -alkylamines for the synthesis of enantiomerically enriched β-substituted amines, entities prevalent in pharmaceutical compounds and used to generate different families of chiral catalysts. We demonstrate that a catalyst system comprising of seemingly competitive Lewis acids, B(CF), and a chiral Mg- or Sc-based complex, promotes the highly enantioselective union of -alkylamines and α,β-unsaturated compounds. An array of δ-amino carbonyl compounds was synthesized under redox-neutral conditions by enantioselective reaction of a -alkylamine-derived enamine and an electrophile activated by the chiral Lewis acid co-catalyst.

B(CF)-Catalyzed -Deuteration of Bioactive Carbonyl Compounds with DO.

An efficient deuteration process of -C-H bonds in various carbonyl-based pharmaceutical compounds has been developed. Catalytic reactions are initiated by the action of Lewis acidic B(CF) and DO, converting a drug molecule into the corresponding boron-enolate. Ensuing deuteration of the enolate by in situ-generated DO-H then results in the formation of -deuterated bioactive carbonyl compounds with up to >98% deuterium incorporation.

Catalytic Deuterium Incorporation within Metabolically Stable β-Amino C-H Bonds of Drug Molecules.

An efficient deuteration process of β-amino C-H bonds in various -alkylamine-based pharmaceutical compounds has been developed. Catalytic reactions begin with the action of Lewis acidic B(CF) and Brønsted basic -alkylamine, converting a drug molecule into the corresponding enamine. The acid/base catalysts also promote the dedeuteration of acetone- to afford a deuterated ammonium ion.

Three-dimensional soft tissue changes according to skeletal changes after mandibular setback surgery by using cone-beam computed tomography and a structured light scanner.

Background: To evaluate the three-dimensional (3D) changes after mandibular setback surgery (MSS) in skeletal Class III malocclusion using cone-beam computed tomography (CBCT) and a structured light-based scanner.

Methods: Twenty-eight adult Korean patients with skeletal Class III malocclusion treated by MSS were evaluated. CBCT and facial scan images were recorded one week before and six months after surgery.

An OMICS-based study of the role of C3dg in keratinocytes: RNA sequencing, antibody-chip array, and bioinformatics approaches.

Previously, we have identified the C3dg protein as an important player in the pathogenesis of atopic dermatitis (AD). In this study, we aimed to identify critical factors associated with C3dg in human keratinocytes based on high-throughput screening (HTS) approaches. We overexpressed C3dg in HaCaT human keratinocytes and conducted serial HTS studies, including RNA sequencing analysis integrated with antibody-chip arrays and implementation of bioinformatics algorithms (PPI mappings).

B(CF)-Catalyzed C-H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant.

An efficient method for the coupling of N-alkylamines with silicon enolates to generate β-amino carbonyl compounds is disclosed. These reactions proceed by activation of α-amino C-H bonds by B(CF), which likely generates a "frustrated" acid/base complex in the presence of large N-alkylamines. The transformation requires no external oxidant and releases hydrosilane as a byproduct.

C-H Functionalization of Amines via Alkene-Derived Nucleophiles through Cooperative Action of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis.

Catalytic transformations of α-amino C-H bonds to afford valuable enantiomerically enriched α-substituted amines, entities that are prevalent in pharmaceuticals and bioactive natural products, have been developed. Typically, such processes are carried out under oxidative conditions and require precious metal-based catalysts. Here, we disclose a strategy for an enantioselective union of N-alkylamines and α,β-unsaturated compounds, performed under redox-neutral conditions, and promoted through concerted action of seemingly competitive Lewis acids, B(CF), and a chiral Mg-PyBOX complex.

Measurement of three-dimensional perioral soft tissue changes in dentoalveolar protrusion patients after orthodontic treatment using a structured light scanner.

Objective: To evaluate the three-dimensional (3D) perioral soft tissue changes after orthodontic treatment in patients with dentoalveolar protrusion using structured light-based scanners.

Materials And Methods: Forty-four Korean adults (19 men and 25 women, 21.4 ± 3.