Department of Chemistry , Fudan University , 2005 Songhu Road , Shanghai , 200438 , China.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering , East China Normal University , Shanghai 200062 , China.
J Am Chem Soc. 2019 May 22;141(20):8110-8115. doi: 10.1021/jacs.9b04332. Epub 2019 May 13.
A highly enantioselective palladium-catalyzed iodine atom transfer cycloisomerization of unactivated alkenes has been developed. This represents the first example of highly enantioselective carboiodination of olefin-tethered aryl iodides, which provides a perfect atom economy method to construct a series of optically active 2,3-dihydrobenzofuran, indolines and chromane bearing an alkyl iodide group in moderate to good yields. Moreover, the use of readily available starting materials, a broad substrate scope, high selectivity, mild reaction conditions, as well as versatile transformation of the product make this approach attractive. The mechanism of this Pd(0)-catalyzed asymmetric carboiodination of alkenes has been investigated with density functional theory.
一种高对映选择性的钯催化碘原子转移环异构化反应已被开发出来。这代表了首例高对映选择性的烯烃键合芳基碘的碳碘键化反应，为构建一系列光学活性的 2,3-二氢苯并呋喃、吲哚啉和色满提供了一种完美的原子经济性方法，产率中等至良好。此外，该方法使用易得的起始原料、广泛的底物范围、高选择性、温和的反应条件以及产物的多功能转化，使其具有吸引力。利用密度泛函理论对该 Pd(0)催化的烯烃不对称碳碘键化反应的机理进行了研究。
