Suzuki–Miyaura Cross-Coupling of Potassium Alkoxyethyltrifluoroborates: Access to Aryl/Heteroarylethyloxy Motifs

• Published in: Journal of organic chemistry Vol. 77; no. 22; pp. 10399 - 10408
• Main Authors: Fleury-Brégeot, Nicolas, Presset, Marc, Beaumard, Floriane, Colombel, Virginie, Oehlrich, Daniel, Rombouts, Frederik, Molander, Gary A
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.11.2012; Amer Chemical Soc
• Subjects: B derivatives; Borates - chemistry; Catalysis; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - chemistry; Molecular Structure; Organic chemistry; Organometalloidal and organometallic compounds; Oxygen - chemistry; Physical Sciences; Potassium - chemistry; Preparations and properties; Science & Technology; BOC-PROTECTED AMINOMETHYLTRIFLUOROBORATE; BORONIC ACID; HYDROBORATION; ETHERS; ARYL; CATALYZED BORYLATION; ALKYLBORONIC ESTERS; DERIVATIVES; C-H BONDS; ALKYL-HALIDES; Suzuki coupling; Potassium compound; Cross reaction; Organic bromine compounds; Aromatic compound; Chemical synthesis; Potassium; Heterocyclic compound
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo3021665

The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and heteroaryl bromides.