Skeletal editing of (hetero) arenes using carbenes

Z Liu, P Sivaguru, Y Ning, Y Wu… - Chemistry–A European …, 2023 - Wiley Online Library
Abstract (Hetero) arenes continue to prove their indispensability in pharmaceuticals,
materials science, and synthetic chemistry. As such, the controllable modification of …

Dearomative ring expansion of thiophenes by bicyclobutane insertion

H Wang, H Shao, A Das, S Dutta, HT Chan, C Daniliuc… - Science, 2023 - science.org
Skeletal ring enlargement is gaining renewed interest in synthetic chemistry and has
recently focused on insertion of one or two atoms. Strategies for heterocyclic expansion …

Skeletal editing of pyridines through atom-pair swap from CN to CC

Q Cheng, D Bhattacharya, M Haring, H Cao… - Nature Chemistry, 2024 - nature.com
Skeletal editing is a straightforward synthetic strategy for precise substitution or
rearrangement of atoms in core ring structures of complex molecules; it enables quick …

Unimolecular Fragment Coupling: A New Bond-Forming Methodology via the Deletion of Atom (s)

R Shimazumi, M Tobisu - JACS Au, 2024 - ACS Publications
Unimolecular fragment coupling (UFC) is defined as a reaction format, wherein atom (s)
located in the middle of a molecule are extruded, and the remaining fragments are coupled …

Ring expansion of indene by photoredox-enabled functionalized carbon-atom insertion

FP Wu, CC Chintawar, R Lalisse, P Mukherjee… - Nature Catalysis, 2024 - nature.com
Skeletal editing has received unprecedented attention as an emerging technology for the
late-stage manipulation of molecular scaffolds. The direct achievement of functionalized …

Dearomatization of pyridines: photochemical skeletal enlargement for the synthesis of 1, 2-diazepines

E Boudry, F Bourdreux, J Marrot… - Journal of the …, 2024 - ACS Publications
In this report, we developed a unified and standardized one-pot sequence that converts
pyridine derivatives into 1, 2-diazepines by inserting a nitrogen atom. This skeletal …

Photochemically mediated ring expansion of indoles and pyrroles with chlorodiazirines: synthetic methodology and thermal hazard assessment

BW Joynson, GR Cumming… - Angewandte Chemie …, 2023 - Wiley Online Library
We demonstrate that arylchlorodiazirines serve as photo‐activated halocarbene precursors
for the selective one‐carbon ring expansion of N‐substituted pyrroles and indoles to the …

Direct Access to Quinazolines and Pyrimidines from Unprotected Indoles and Pyrroles through Nitrogen Atom Insertion

JC Reisenbauer, ASK Paschke, J Krizic, BB Botlik… - Organic …, 2023 - ACS Publications
Recent advances in single-atom insertion reactions have opened up new synthetic
approaches for molecular diversification. Developing innovative strategies to directly …

Dearomative insertion of fluoroalkyl carbenes into azoles leading to fluoroalkyl heterocycles with a quaternary center

L Li, Y Ning, H Chen, Y Ning, P Sivaguru… - Angewandte Chemie …, 2024 - Wiley Online Library
The skeletal ring expansion of heteroarenes through carbene insertion is gaining popularity
in synthetic chemistry. Efficient strategies for heterocyclic ring expansion to access …

One‐Carbon Ring Expansion of Indoles and Pyrroles: A Straightforward Access to 3‐Fluorinated Quinolines and Pyridines

H Guo, S Qiu, P Xu - Angewandte Chemie International Edition, 2024 - Wiley Online Library
Fluorinated quinolines and pyridines are prevalent pharmacophores, yet their synthesis is
often challenging. Herein, we demonstrate that dibromofluoromethane as …