Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.
J Am Chem Soc. 2016 Aug 10;138(31):9763-6. doi: 10.1021/jacs.6b05216. Epub 2016 Jul 26.
A cascade cyanation/diborylation of terminal allenes proceeds efficiently with copper catalysis using bis(pinacolato)diboron (B2Pin2) and N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as reagents. Mechanistic studies suggest that the process proceeds through cyanoborylation of the substituted π-system of the allene followed by hydroboration of the remaining π-component. A wide array of product derivatives may be accessed through site-selective cross-couplings and N-bromosuccinimide-promoted heteroarylations as well as standard oxidative and reductive conversions of the initially obtained adducts.
末端丙二烯的级联氰化/双硼化反应在铜催化下，使用双(频哪醇)二硼（B2Pin2）和 N-氰基-N-苯基-p-甲基苯磺酰胺（NCTS）作为试剂，可高效进行。机理研究表明，该过程通过丙二烯取代的π-体系的氰基硼化，然后剩余的π-组分的硼氢化进行。通过选择性交叉偶联和 N-溴代琥珀酰亚胺促进的杂芳基化反应以及初始获得的加合物的标准氧化和还原转化，可以获得多种产物衍生物。
