Suzuki-Miyaura Cross-Coupling of Potassium Organoborates with 6-Sulfonate Benzimidazoles Using Microwave Irradiation

This article focuses on the utility of organotrifluoroborate salts as coupling partners for Suzuki–Miyaura cross‐coupling with 4‐nitro‐6‐triflyl benzimidazoles using microwave irradiation. The C–C bond formation at the 6‐position of the electron‐rich 1‐,4‐,6‐trisubstituted benzimidazole core is chal...

Full description

Saved in:
Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 50; no. S1; pp. E166 - E173
Main Authors Jain, Prashi, Yi, Shuyan, Flaherty, Patrick Thomas
Format Journal Article
LanguageEnglish
Published Hoboken Blackwell Publishing Ltd 01.02.2013
Wiley Subscription Services, Inc
Subjects
Potassium
Online AccessGet full text

Cover

More Information
Summary:This article focuses on the utility of organotrifluoroborate salts as coupling partners for Suzuki–Miyaura cross‐coupling with 4‐nitro‐6‐triflyl benzimidazoles using microwave irradiation. The C–C bond formation at the 6‐position of the electron‐rich 1‐,4‐,6‐trisubstituted benzimidazole core is challenging and was not achievable via Kumada, Negishi, Stille, or Heck coupling strategies. Yields of 37–70% could be obtained via palladium coupling strategies utilizing potassium benzyl trifluoroborates as the organometallic coupling partner.
Bibliography:ArticleID:JHET1109
istex:E21138299E451485B197CBC46B5BE74E44D3DE91
NSF equipment grant - No. NMR: CHE 0614785
NIH (NINDS) - No. 1R15NS057772
ark:/67375/WNG-CKXNXGTT-8
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.1109