Strain-release photocatalysis

P Bellotti, F Glorius - Journal of the American Chemical Society, 2023 - ACS Publications
The concept of strain in organic compounds is as old as modern organic chemistry and was
initially introduced to justify the synthetic setbacks along the synthesis of small ring systems …

Three-dimensional saturated C(sp3)-rich bioisosteres for benzene

J Tsien, C Hu, RR Merchant, T Qin - Nature Reviews Chemistry, 2024 - nature.com
Benzenes, the most ubiquitous structural moiety in marketed small-molecule drugs, are
frequently associated with poor 'drug-like'properties, including metabolic instability, and poor …

Photocatalyzed [2σ+ 2σ] and [2σ+ 2π] Cycloadditions for the Synthesis of Bicyclo [3.1. 1] heptanes and 5-or 6-Membered Carbocycles

TVT Nguyen, A Bossonnet, MD Wodrich… - Journal of the American …, 2023 - ACS Publications
We report the use of photocatalysis for the homolytic ring-opening of carbonyl
cyclopropanes. In contrast to previous studies, our approach does not require a metal …

Silver‐Catalyzed Dearomative [2π+ 2σ] Cycloadditions of Indoles with Bicyclobutanes: Access to Indoline Fused Bicyclo [2.1. 1] hexanes

L Tang, Y Xiao, F Wu, JL Zhou, TT Xu… - Angewandte Chemie …, 2023 - Wiley Online Library
Abstract Bicyclo [2.1. 1] hexanes (BCHs) are becoming ever more important in drug design
and development as bridged scaffolds that provide underexplored chemical space, but are …

A Photochemical Strategy for the Conversion of Nitroarenes into Rigidified Pyrrolidine Analogues

E Matador, MJ Tilby, I Saridakis, M Pedrón… - Journal of the …, 2023 - ACS Publications
Bicyclic amines are important motifs for the preparation of bioactive materials. These species
have well-defined exit vectors that enable accurate disposition of substituents toward …

Silver (i)-catalyzed synthesis of cuneanes from cubanes and their investigation as isosteres

E Smith, KD Jones, L O'Brien, SP Argent… - Journal of the …, 2023 - ACS Publications
Bridged or caged polycyclic hydrocarbons have rigid structures that project substituents into
precise regions of 3D space, making them attractive as linking groups in materials science …

1, 2-Disubstituted bicyclo [2.1. 1] hexanes as saturated bioisosteres of ortho-substituted benzene

A Denisenko, P Garbuz, Y Makovetska… - Chemical …, 2023 - pubs.rsc.org
Bicyclo [2.1. 1] hexanes have been synthesized, characterized, and biologically validated as
saturated bioisosteres of the ortho-substituted benzene ring. The incorporation of the 1, 2 …

Synthesis of polysubstituted bicyclo [2.1. 1] hexanes enabling access to new chemical space

M Reinhold, J Steinebach, C Golz, JCL Walker - Chemical Science, 2023 - pubs.rsc.org
Saturated bridged-bicyclic compounds are currently under intense investigation as building
blocks for pharmaceutical drug design. However, the most common methods for their …

A General Three-Component Alkyl Petasis Boron–Mannich Reaction

C Hu, J Tsien, SJ Chen, M Kong… - Journal of the …, 2024 - ACS Publications
Aryl amines are one of the most common moieties in biologically active molecules, and
approximately 37% of drug candidates contain aromatic amines. Recent advancements in …

Exploring cuneanes as potential benzene isosteres and energetic materials: Scope and mechanistic investigations into regioselective rearrangements from cubanes

JY Son, S Aikonen, N Morgan… - Journal of the …, 2023 - ACS Publications
Cuneane is a strained hydrocarbon that can be accessed via metal-catalyzed isomerization
of cubane. The carbon atoms of cuneane define a polyhedron of the C 2 v point group with …