Copper-Catalyzed Benzylic C–H Cross-Coupling Enabled by Redox Buffers: Expanding Synthetic Access to Three-Dimensional Chemical Space

SJ Chen, SW Krska, SS Stahl - Accounts of chemical research, 2023 - ACS Publications
Conspectus Cross-coupling methods are the most widely used synthetic methods in
medicinal chemistry. Existing reactions are dominated by methods such as amide coupling …

Direct Benzylic C− H Etherification Enabled by Base‐Promoted Halogen Transfer

KI Bone, TR Puleo, MD Delost, Y Shimizu… - Angewandte …, 2024 - Wiley Online Library
We disclose a benzylic C− H oxidative coupling reaction with alcohols that proceeds through
a synergistic deprotonation, halogenation and substitution sequence. The combination of …

C(sp3)−H (N‐Phenyltetrazole)thiolation as an Enabling Tool for Molecular Diversification

AKZ Zachmann, JA Drappeau, S Liu… - Angewandte …, 2024 - Wiley Online Library
Methods enabling the broad diversification of C (sp3)− H bonds from a common
intermediate are especially valuable in chemical synthesis. Herein, we report a site …

Radical chlorination of non-resonant heterobenzylic C‒H bonds and high-throughput diversification of heterocycles

DL Golden, KM Flynn, S Aikonen, CM Hanneman… - Chem, 2024 - cell.com
Site-selective functionalization of the heterobenzylic C (sp 3)–H bonds of pyridines and
related heteroaromatic compounds presents challenges associated with the basic nitrogen …

C3-Functionalization of indoles with α-heteroaryl-substituted methyl alcohols

EJ Pazur, NR Tasker, P Wipf - Organic & Biomolecular Chemistry, 2023 - pubs.rsc.org
The transition metal-free Cs2CO3/Oxone®-mediated C3-alkylation of indoles proceeds in
moderate to high yields with a variety of C4–C7 functionalized indoles and is applicable to 2 …

Synthesis of benzenes from pyridines via N to C switch

A Conboy, MF Greaney - Chem, 2024 - cell.com
The skeletal editing of heteroarenes introduces new disconnections to the chemistry lexicon,
enabling the interconversion of ring systems via selective breaking/re-making of the carbon …

Harnessing the Power of C–H Functionalization Chemistry to Accelerate Drug Discovery

B Li, S Tyagarajan, KD Dykstra, T Cernak, P Vachal… - Synlett, 2024 - thieme-connect.com
The field of C–H functionalization chemistry has experienced rapid growth in the past twenty
years, with increasingly powerful applications in organic synthesis. Recognizing the …

Site-selective benzylic C–H hydroxylation in electron-deficient azaheterocycles

M Kaur, JC Cooper, JF Van Humbeck - Organic & Biomolecular …, 2024 - pubs.rsc.org
Benzylic C–H bonds can be converted into numerous functional groups, often by
mechanisms that involve hydrogen atom transfer as the key bond breaking step. The …

Dirhodium-catalyzed one-step cascade intermolecular 1, 4-diamination via cyclopropanation

Q Yang, X Liu, S Qin, Y Wang - Organic Chemistry Frontiers, 2024 - pubs.rsc.org
This work presents a novel dirhodium-catalyzed method for the conversion of aromatic
hydrocarbons to 1, 4-diamines using N-fluorobenzenesulfonimide (NFSI) as the nitrogen …

Stability and reactivity of alkylidene dihydropyridines

M Puzhistky, E Pradhan, A Nikolaev, T Zeng… - Organic & …, 2024 - pubs.rsc.org
Alkylidene dihydropyridines (ADHPs) are electron-rich nucleophilic intermediates that can
be readily prepared by dearomatization of 4-alkylpyridines using chloroformate reagents …