Energy transfer photocatalysis: exciting modes of reactivity

S Dutta, JE Erchinger, F Strieth-Kalthoff… - Chemical Society …, 2024 - pubs.rsc.org
Excited (triplet) states offer a myriad of attractive synthetic pathways, including
cycloadditions, selective homolytic bond cleavages and strain-release chemistry …

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 …

Intermolecular [2π+2σ]-photocycloaddition enabled by triplet energy transfer

R Kleinmans, T Pinkert, S Dutta, TO Paulisch, H Keum… - Nature, 2022 - nature.com
For more than one century, photochemical [2+ 2]-cycloadditions have been used by
synthetic chemists to make cyclobutanes, four-membered carbon-based rings. In this …

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 …

Bioisosteres of the phenyl ring: recent strategic applications in lead optimization and drug design

MAM Subbaiah, NA Meanwell - Journal of Medicinal Chemistry, 2021 - ACS Publications
The benzene moiety is the most prevalent ring system in marketed drugs, underscoring its
historic popularity in drug design either as a pharmacophore or as a scaffold that projects …

General access to cubanes as benzene bioisosteres

MP Wiesenfeldt, JA Rossi-Ashton, IB Perry, J Diesel… - Nature, 2023 - nature.com
The replacement of benzene rings with sp 3-hybridized bioisosteres in drug candidates
generally improves pharmacokinetic properties while retaining biological activity,,,–. Rigid …

Pyridine-boryl radical-catalyzed [2π+ 2σ] cycloaddition of bicyclo [1.1. 0] butanes with alkenes

Y Liu, S Lin, Y Li, JH Xue, Q Li, H Wang - ACS Catalysis, 2023 - ACS Publications
Bicyclo [2.1. 1] hexanes (BCHs) represent an intriguing class of structurally rigid
hydrocarbons that can serve as the bioisosteres of benzenoids in medicinal chemistry …

Synthesis of meta-substituted arene bioisosteres from [3.1.1]propellane

N Frank, J Nugent, BR Shire, HD Pickford, P Rabe… - Nature, 2022 - nature.com
Small-ring cage hydrocarbons are popular bioisosteres (molecular replacements) for
commonly found para-substituted benzene rings in drug design. The utility of these cage …

Synthesis of polysubstituted 2-oxabicyclo [2.1. 1] hexanes via visible-light-induced energy transfer

Y Liang, R Kleinmans, CG Daniliuc… - Journal of the American …, 2022 - ACS Publications
Synthesis of bicyclic scaffolds has attracted growing interest because they are of high
importance in modern pharmaceutical development. Here we report a strategy to access …

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 …