Direct α-Arylation of Ethers through the Combination of Photoredox-Mediated CH Functionalization and the Minisci Reaction†
Dr. Jian Jin
Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544 (USA) http://www.princeton.edu/chemistry/macmillan/
Search for more papers by this authorCorresponding Author
Prof. Dr. David W. C. MacMillan
Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544 (USA) http://www.princeton.edu/chemistry/macmillan/
Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544 (USA) http://www.princeton.edu/chemistry/macmillan/Search for more papers by this authorDr. Jian Jin
Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544 (USA) http://www.princeton.edu/chemistry/macmillan/
Search for more papers by this authorCorresponding Author
Prof. Dr. David W. C. MacMillan
Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544 (USA) http://www.princeton.edu/chemistry/macmillan/
Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544 (USA) http://www.princeton.edu/chemistry/macmillan/Search for more papers by this authorThe authors are grateful for financial support provided by the NIH General Medical Sciences (Grant NIHGMS (R01 GM103558-03)) and gifts from Merck, Amgen, Abbvie, and BMS.
Abstract
The direct α-arylation of cyclic and acyclic ethers with heteroarenes has been accomplished through the design of a photoredox-mediated CH functionalization pathway. Transiently generated α-oxyalkyl radicals, produced from a variety of widely available ethers through hydrogen atom transfer (HAT), were coupled with a range of electron-deficient heteroarenes in a Minisci-type mechanism. This mild, visible-light-driven protocol allows direct access to medicinal pharmacophores of broad utility using feedstock substrates and a commercial photocatalyst.
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