Palladium-Catalyzed Direct C-H Arylation of Isoxazoles at the 5-Position

Masashi Shigenobu; Kazuhiro Takenaka; Hiroaki Sasai

doi:10.1002/anie.201504552

Palladium-Catalyzed Direct C-H Arylation of Isoxazoles at the 5-Position

Angew Chem Int Ed Engl. 2015 Aug 10;54(33):9572-6. doi: 10.1002/anie.201504552. Epub 2015 Jun 30.

Authors

Masashi Shigenobu¹, Kazuhiro Takenaka², Hiroaki Sasai³

Affiliations

¹ The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047 (Japan).
² The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047 (Japan). takena@sanken.osaka-u.ac.jp.
³ The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047 (Japan). sasai@sanken.osaka-u.ac.jp.

PMID: 26130462
DOI: 10.1002/anie.201504552

Abstract

A palladium-catalyzed direct arylation of isoxazoles with aryl iodides has been achieved. The C-H bond at the 5-position is activated selectively to give coupling products in moderate to good yields. This direct arylation was applied to the synthesis of a spiro-type chiral ligand, which proved to be most effective to the palladium-catalyzed tandem cyclization of a dialkenyl alcohol.

Keywords: CH activation; arylation; cross-coupling; heterocycles; palladium.