A General Photocatalytic Route to Prenylation. Issue 10 (22nd May 2019)

• Record Type: Journal Article
• Authors: Rathnayake, Manjula D.; Weaver, Jimmie D.
• Other Names: Masson Géraldine guestEditor.; König Burkhard guestEditor.; Yoon Tehshik guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 10(2020)
• Page Start: 1433
• Page End: 1438
• Publication Date: 2019-05-22
• Subjects: Prenylation -- Radicals -- Sulfones -- Photocatalysis -- Beta scission; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900356
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Prenylation is an essential reaction on which nature relies to modify properties of molecules and build terpenoids, but remains a challenging chemical reaction. Aiming to capitalize on recent advances in photocatalysis to easily and cleanly generate a broad range of carbon based radicals, we have developed a prenyl transfer reagent that is captured by transiently generated radicals. The reagent can be made in bulk, is bench stable, and broadly applicable such that it can be used with existing photocatalytic methods with very few changes to reaction conditions. Ultimately, this provides a true drop‐in solution for prenylation, expanding the scope of substrates that can be readily prenylated. Abstract : A new bench stable reagent that is easily synthesized and handled is investigated for its use in radical prenylation of diverse organic molecules. It has demonstrated high functional group compatibility and can be used with numerous photocatalytic methods to give prenylated products from aryl iodides, bromides, anilines, thiols and alkyl halides.