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Forming Benzylic Iodides via a Nickel Catalyzed Diastereoselective Dearomative Carboiodination Reaction of Indoles
Author(s) -
Marchese Austin D.,
Lind Florian,
Mahon Áine E.,
Yoon Hyung,
Lautens Mark
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201900659
Subject(s) - chemistry , intramolecular force , catalysis , nickel , indole test , combinatorial chemistry , reactivity (psychology) , ligand (biochemistry) , alkyl , metal , organic chemistry , medicinal chemistry , medicine , biochemistry , alternative medicine , receptor , pathology
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.