Palladium‐Catalyzed Directed para C−H Functionalization of Phenols. Issue 27 (9th May 2016)

• Record Type: Journal Article
• Authors: Patra, Tuhin; Bag, Sukdev; Kancherla, Rajesh; Mondal, Anirban; Dey, Aniruddha; Pimparkar, Sandeep; Agasti, Soumitra; Modak, Atanu; Maiti, Debabrata
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 27(2016)
• Page Start: 7751
• Page End: 7755
• Publication Date: 2016-05-09
• Subjects: C−H activation -- olefination -- palladium -- silicon -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201601999
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Various practical methods for the selective C−H functionalization of the ortho and recently also of the meta position of an arene have already been developed. Following our recent development of the directing‐group‐assisted para C−H functionalization of toluene derivatives, we herein report the first remote para C−H functionalization of phenol derivatives by using a recyclable silicon‐containing biphenyl‐based template. The effectiveness of this strategy was illustrated with different synthetic elaborations and by the synthesis of various phenol‐based natural products. Abstract : The template‐assisted para C−H olefination of phenol derivatives was enabled by a silicon‐containing directing group (DG; see scheme) in combination with a palladium catalyst. This method was also applied to the synthesis of different natural products.