Pentafluorohalobenzene (C<sub>6</sub>F<sub>5</sub>X) as Iodine or Bromine Transfer Reagents for Synthesis of Disubstituted Pyridines
We report pentafluorohalobenzene (C<sub>6</sub>F<sub>5</sub>I and C<sub>6</sub>F<sub>5</sub>Br) as an iodine or bromine transfer reagent for the generation of both electron-rich and electron-poor (hetero)aryl iodides and bromides with excellent chemo/regio selectivity in up to 95% yields. Continuous flow synthesis proved to be advantageous for this transformation. The iodine or bromine transfer occurs through treatment with in situ-generated (hetero)aryl Grignard reagents derived from aryl halides with C<sub>6</sub>F<sub>5</sub>I or C<sub>6</sub>F<sub>5</sub>Br. The resulting iodo- and chloro/bromo-pyridines were further transformed into bis-substituted pyridines through subsequent chemoselective coupling reactions.
Authors
- Venkatarathnam Nasipireddy
- Chris H. Senanayake (ORCID: https://orcid.org/0009-0009-3170-0687)
- Mohammed Sharique (ORCID: https://orcid.org/0000-0002-4528-4807)
- Lalitha Gummidi (ORCID: https://orcid.org/0000-0002-1357-2468)
- Omkar Revu
- Zhirui Wang (ORCID: https://orcid.org/0000-0003-2877-0384)
- Lalith P. Samankumara
- Anji Chen (ORCID: https://orcid.org/0000-0002-8943-9663)
- Rajasekar Reddy Annapureddy (ORCID: https://orcid.org/0000-0001-5855-4688)
- R. Sridhar (ORCID: https://orcid.org/0000-0003-4869-9511)
- Madhusudhan Reddy Gadi (ORCID: https://orcid.org/0000-0003-3668-4646)
- Praveen Kumar Gajula (ORCID: https://orcid.org/0009-0008-5051-4612)
- Maksim P. Vasilev (ORCID: https://orcid.org/0000-0001-9076-7851)
- Jonathan M. Bietsch
- Shada Arun Dixith Reddy (ORCID: https://orcid.org/0000-0002-0672-7441)
- Srinivas Achanta (ORCID: https://orcid.org/0009-0003-7334-1965)
- Gopal Sirasani
- Sailu Munnuri (ORCID: https://orcid.org/0000-0001-5675-6032)
- Manasa Mamunooru
- Raju Bandu
- Srinivasarao Tenneti (ORCID: https://orcid.org/0000-0002-6687-8348)
- Santhosh Reddy Naini (ORCID: https://orcid.org/0000-0001-7825-5810)
- Aravind S. Gangu (ORCID: https://orcid.org/0009-0000-2234-7994)
- Bo Qu (ORCID: https://orcid.org/0000-0001-7347-0108)
- Nageswara Rao Kalikinidi (ORCID: https://orcid.org/0000-0002-5378-9207)
- V. S. Tiwari
- Shanika M. P. Gamage
- Rahul Shingare
- Sameera Arachchige
Institutions
- Green Chemistry (PL)
- The College of New Jersey (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-09-18
- DOI
- https://doi.org/10.1021/acs.joc.5c01065
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00