Translation of Nickel-Catalyzed C(sp<sup>2</sup>)–C(sp<sup>3</sup>) Cross-Electrophile Coupling to Non-Amide Solvents
The cross-electrophile coupling of organobromides is widely utilized in organic synthesis but generally requires undesirable amide solvents (e.g., DMF, DMA, and NMP). We report that the combination of a strongly donating, bidentate nitrogen ligand, LiI, and 4-picoline enables coupling in a variety of alcohol, ester, and ethereal solvents at up to 50 g scale. An improved synthesis of the optimal ligand, 4,4'-bis(dimethylamino)-2,2'-bipyridine, is also reported on the basis of the reductive homocoupling of 4-dimethylamino-2-chloropyridine.
Authors
- Julianna M. Mouat (ORCID: https://orcid.org/0000-0002-3976-3676)
- Brett D. Akana‐Schneider (ORCID: https://orcid.org/0000-0002-2249-3809)
- Daniel J. Weix (ORCID: https://orcid.org/0000-0002-9552-3378)
- Bin Wu (ORCID: https://orcid.org/0000-0002-9761-2139)
- Michelle E. Akana (ORCID: https://orcid.org/0000-0002-1148-7059)
- Sisi Zhang (ORCID: https://orcid.org/0000-0002-3852-4796)
Institutions
- Novartis (Switzerland) (CH)
- University of Wisconsin–Madison (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c01011
- Citations
- 1
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Novartis
- University of Wisconsin-Madison
- National Institute of General Medical Sciences
- Division of Chemistry