Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions
Patrick S. Fier* and Kevin M. Maloney*
*Department of Process & Analytical Chemistry, Merck Research
Laboratories, 126 East Lincoln Avenue, Rahway, New Jersey 07065, United States, Email:
patrick.fier
merck.com, kevin_maloneymerck.com
P. S. Fier, K. M. Maloney, Org. Lett., 2016, 18, 2244-2247.
DOI: 10.1021/acs.orglett.6b00876
Abstract
In a practical method for the synthesis of phenols from electron-deficient haloarenes and heteroarenes, the products are formed from acetohydroxamic acid as the hydroxide source via a novel SNAr reaction/Lossen rearrangement sequence. Notably, these reactions occur under mildly basic conditions, employ inexpensive and air-stable reagents, require no special handling, and form products in high yields in the presence of various functionality.
see article for more examples
Lossen Rearrangement and Proposed Application toward the Synthesis of Phenols
P. S. Fier, K. M. Maloney, Org. Lett., 2017, 19, 3033-3036.
Key Words
ID: J54-Y2016
