Frame‐Shifted Synthesis of Oligoheterocycles as a Platform for Molecular Design

K Kane A. C. Bastick (Department of Chemistry University of Toronto Toronto ON M5S 3H6 Canada) C Caleb E. Griesbach (Department of Chemistry University of Toronto Toronto ON M5S 3H6 Canada) B Ben Zhen Huang (Davenport Research Laboratories Department of Chemistry University of Toronto Toronto Ontario Canada) M Morgan J. Cordell (Department of Chemistry University of Toronto Toronto ON M5S 3H6 Canada) Y Yang (Daniel) Ou (Department of Chemistry University of Toronto Toronto ON M5S 3H6 Canada) A Alán Aspuru‐Guzik (Department of Chemistry University of Toronto Toronto ON M5S 3H6 Canada) A Andrei K. Yudin (Davenport Research Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada)

Abstract

Abstract Chemists continue to develop strategies that leverage abundant feedstocks to accelerate the production of medicines, agrochemicals, and materials. Oligoheterocycles are a broad class of molecules that span these disciplines. Cross‐coupling strategies are commonly used to assemble oligoheterocycles; however, these methods can be challenging and often rely on precious metal catalysts and building blocks whose production entails significant environmental and economic costs. We present a strategy for the iterative construction of oligoheterocycles that leverages sustainable building blocks designed around high‐oxidation‐state carbon. By utilizing feedstocks from the base of the chemical supply chain, we generate bifunctional building blocks that chemoselectively engage with a variety of partners through simple condensation manifolds. This approach has enabled the creation of novel scaffolds previously inaccessible by conventional means, exemplifying sustainable design strategies.

Article Details

Volume / Issue Vol. 65, Issue 2
Published January 09, 2026
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (7)

K

Kane A. C. Bastick

Department of Chemistry University of Toronto Toronto ON M5S 3H6 Canada

C

Caleb E. Griesbach

Department of Chemistry University of Toronto Toronto ON M5S 3H6 Canada

B

Ben Zhen Huang

Davenport Research Laboratories Department of Chemistry University of Toronto Toronto Ontario Canada

M

Morgan J. Cordell

Department of Chemistry University of Toronto Toronto ON M5S 3H6 Canada

Y

Yang (Daniel) Ou

Department of Chemistry University of Toronto Toronto ON M5S 3H6 Canada

A

Alán Aspuru‐Guzik

Department of Chemistry University of Toronto Toronto ON M5S 3H6 Canada

A

Andrei K. Yudin

Davenport Research Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada