Department of Process & Analytical Chemistry, Merck Research Laboratories , 126 East Lincoln Avenue, Rahway, New Jersey 07065, United States.
Org Lett. 2016 May 6;18(9):2244-7. doi: 10.1021/acs.orglett.6b00876. Epub 2016 Apr 14.
A high-yielding and practical method for the synthesis of phenols from electron-deficient haloarenes and heteroarenes has been developed. The products are formed from acetohydroxamic acid as the hydroxide source via a novel SNAr reaction/Lossen rearrangement sequence. Notably, these reactions employ inexpensive and air-stable reagents, require no special handling, occur under mildly basic conditions, and form products in high yields in the presence of electrophilic and protic functionality. The utility of this methodology is demonstrated by the high-yielding hydroxylation of two base-sensitive complex substrates.
已经开发出一种从缺电子卤代芳烃和杂芳烃合成酚的高产率、实用方法。产物是通过新型的SNAr 反应/Lossen 重排序列，由乙酰羟肟酸作为氢氧根源形成的。值得注意的是，这些反应使用廉价且稳定的试剂，无需特殊处理，在温和的碱性条件下进行，并在存在亲电和亲核官能团时以高产率形成产物。该方法的实用性通过对两种对碱敏感的复杂底物的高产率羟化反应得到了证明。
