醌与硼酸的实用 C-H 官能化。
Practical C-H functionalization of quinones with boronic acids.
机构信息
Department of Chemistry and Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
出版信息
J Am Chem Soc. 2011 Mar 16;133(10):3292-5. doi: 10.1021/ja111152z. Epub 2011 Feb 22.
Abstract
A direct functionalization of a variety of quinones with several boronic acids has been developed. This scalable reaction proceeds readily at room temperature in an open flask using inexpensive reagents: catalytic silver(I) nitrate in the presence of a persulfate co-oxidant. The scope with respect to quinones is broad, with a variety of alkyl- and arylboronic acids undergoing efficient cross-coupling. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone. This method has been applied to complex substrates, including a steroid derivative and a farnesyl natural product.
摘要
已经开发出一种可将多种苯醌与多种硼酸直接官能化的方法。该可扩展的反应在室温下在开放烧瓶中使用廉价试剂：催化硝酸银（I）和过硫酸盐共氧化剂进行，反应易于进行。就苯醌而言，其适用范围很广，各种烷基和芳基硼酸都能进行有效的交叉偶联。该机理被认为是通过亲核自由基加成到苯醌上，然后对生成的二氢醌进行原位氧化。该方法已应用于复杂的底物，包括甾体衍生物和法呢基天然产物。
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