School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
Published: August 2016
AI Article Synopsis
Article Abstract
The reaction of chiral (hetero)aryl benzyl sulfoxides with Grignard reagents affords enantiomerically pure diarylalkanes in up to 98 % yield and greater than 99.5 % enantiomeric excess. This ligand coupling reaction is tolerant to multiple substitution patterns and provides access to diverse areas of chemical space in three operationally simple steps from commercially available reagents. This strategy provides orthogonal access to electron-deficient heteroaromatic compounds, which are traditionally synthesized by transition metal catalyzed cross-couplings, and circumvents common issues associated with proto-demetalation and β-hydride elimination.
The microbial UbiX-UbiD system facilitates the reversible (de)carboxylation of alpha, beta-unsaturated carboxylic acids, including aromatic compounds. The direct C-H carboxylation presents an attractive method for functionalisation and carbon capture but is difficult to achieve under mild conditions. Hence, UbiD-mediated Csp2-H activation can serve as a versatile tool for developing new biocatalytic routes to transform aryl or alkene compounds and carbon dioxide into valuable commodity chemicals.
State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, China.
- Ketone-to-alkene transformations are important in organic chemistry, and recent nickel-catalyzed reductive alkenylation reactions show promise for creating a variety of alkenes using different functional groups.
- The authors' research started with coupling α-chloroboronates, then expanded to include a range of radical-inactive compounds, leading to the development of new strategies for cross-selectivity in various chemical reactions.
- These advancements enable efficient synthesis of valuable products, including functionalized cycloalkenes and diverse alkenes, by broadening the types of enol derivatives used in the reactions, making the approach more accessible and practical.
Triceptides are a class of ribosomally synthesized and post-translationally modified peptides defined by an aromatic C(sp) to Cβ(sp) bond. The Gly-rich repeat family of triceptide maturases (TIGR04261) are paired with precursor peptides (TIGR04260) containing a Gly-rich core peptide. These maturases are prevalent in cyanobacteria and catalyze cyclophane formation on multiple Ω1-X2-X3 motifs (Ω1 = Trp and Phe) of the Gly-rich precursor peptide.
Organosilanes have secured a special place in the synthetic world for several decades. However, among them, allylsilanes are a choice reagent for organic chemists to develop novel organic transformations. In recent years researchers have proved that visible-light photoredox catalysis has emerged as one of the most mild, sustainable, straightforward, and efficient strategies to construct simple to complex molecules with or without enantioselectivity.
Herein, we report the Cu-complex catalyzed, native functional group-assisted, and TFA/NMF additives promoted (phenylsulfonyl)difluoromethylation of vinylic C(sp )-H bond of acrylamides. Using our in-home designed reagent, this reaction enables the construction of the C(sp )-CF SO Ph bond from simple C-H bond activation by copper catalysis under mild reaction conditions with total Z-selectivity. The versatility of utilized fluorinated group was illustrated by its conversion into value-added CF moieties as well as the remarkable =CHF residue.
