Acid Fluorides as Acyl Electrophiles in Suzuki–Miyaura Coupling. Issue 29 (10th August 2017)

• Record Type: Journal Article
• Authors: Ogiwara, Yohei; Sakino, Daisuke; Sakurai, Yuka; Sakai, Norio
• Is Part Of: European journal of organic chemistry. Issue 29(2017)
• Page Start: 4324
• Page End: 4327
• Publication Date: 2017-08-10
• Subjects: Cross‐coupling -- Ketones -- Acyl fluorides -- Boronic acids -- Palladium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700917
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The first palladium‐catalyzed construction of ketones through Suzuki–Miyaura reaction by using acid fluorides is described. In contrast to typical acyl electrophiles such as acid chlorides, acid fluorides are uncommon acyl electrophiles to use in boron‐based coupling reactions, probably due to a high level of stability toward nucleophiles. This first attempt to use acid fluorides as a coupling partner with boronic acids allowed highly functional group tolerance and a wide substrate scope while affording various ketones in effective yields. Abstract : Acyl fluorides as Suzuki electrophiles: Acyl fluorides functioned as a coupling partner in a Suzuki–Miyaura reaction. This transformation effectively provided a wide range of symmetrical and unsymmetrical ketones including aryl‐, heteroaryl‐, alkenyl‐, and alkyl frameworks.