A Simplified, One-Pot, Procedure for the Deoxygenative Alkylation of Aryl Bromides
Advancements in the field of C(sp<sup>2</sup>)-C(sp<sup>3</sup>) cross-coupling using alcohols as feedstocks have resulted in widespread adoption in analogue synthesis. Using high-throughput experimentation, an in situ alcohol activation with N-heterocyclic carbenes in DMA was discovered. Validation of the optimized, workup-free conditions suggested equivalent or greater reactivity to conditions where the alcohol is activated separately. The methodology was tested with a set of polar alcohols with drug-like properties, resulting in isolated product in 45/48 reactions.
Authors
- James Mulhearn (ORCID: https://orcid.org/0009-0002-0846-112X)
- Justin B. Diccianni (ORCID: https://orcid.org/0009-0005-2922-6868)
- Shane Plunkett (ORCID: https://orcid.org/0000-0002-5825-8085)
- Soo Young Choi (ORCID: https://orcid.org/0000-0002-4424-6729)
Institutions
- Johnson & Johnson (United States) (US)
- Discovery Centre (CA)
- Analytical Engineering (United States) (US)
- Discovery Laboratories (United States) (US)
- Johnson & Johnson (Israel) (IL)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-10-09
- DOI
- https://doi.org/10.1021/acs.orglett.5c03643
- Citations
- 2
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.07