Forming Benzylic Iodides via a Nickel Catalyzed Diastereoselective Dearomative Carboiodination Reaction of Indoles

Angewandte Chemie
Austin D MarcheseMark Lautens

Abstract

A diastereoselective dearomative carboiodination reaction is reported. We report a novel metal-catalyzed approach to install reactive secondary benzylic iodides. Utilizing the unique reactivity of nickel, we have expanded the carboiodination reaction to non-activated aromatic double bonds forming a previously unattainable class of iodides. We also report a broadly applicable method to avoid the use of a metallic reducing agent by utilizing an alkyl phosphite as the ligand. The reaction is thought to proceed through a syn intramolecular carbonickelation across a 2-substituted indole followed by a diastereoretentive reductive elimination of the carbon-iodine bond. The complex iodinated indolines generated in the reaction were obtained in moderate to good yields and good to excellent diastereoselectivity. The products were easily functionalized by a variety of synthetic methods.

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Citations

Feb 29, 2020·Chemical Communications : Chem Comm·Jian WangYongjia Shang
Oct 10, 2020·Chemical Science·Ping YangShu-Li You
Oct 31, 2020·Chemistry : a European Journal·Risto Savela, Carolina Méndez-Gálvez
Jan 9, 2021·Angewandte Chemie·Ren-Xiao LiangYi-Xia Jia
Mar 2, 2021·Angewandte Chemie·Austin D MarcheseMark Lautens
Jul 25, 2020·Accounts of Chemical Research·Austin D MarcheseMark Lautens
Sep 29, 2021·Journal of the American Chemical Society·Grace L TrammelM Kevin Brown

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