Cascade Copper-Catalyzed 1,2,3-Trifunctionalization of Terminal Allenes
Cascade Copper-Catalyzed 1,2,3-Trifunctionalization of Terminal Allenes
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级联铜催化末端八烯的 1,2,3-三官能化
DOI：
10.1021/jacs.6b05216
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发表时间：
2016
影响因子：
15
通讯作者：
Montgomery, John
中科院分区：
文献类型：
--
作者：
Zhao, Wanxiang;Montgomery, John
以双频哪醇基二硼（B2 Pin 2）和N-氰基-N-苯基-对甲基苯磺酰胺（NCTS）为试剂，在铜催化下，进行了末端联烯的级联氰化/二硼化反应。机理研究表明，该过程通过联烯的取代π-系统的氰基硼化，然后剩余π-组分的硼氢化来进行。通过位点选择性交叉偶联和N-溴代琥珀酰亚胺促进的杂芳基化以及最初获得的加合物的标准氧化和还原转化，可以获得广泛的产物衍生物。
A cascade cyanation/diborylation of terminal allenes proceeds efficiently with copper catalysis usingbis(pinacolato)diboron (B2Pin2) andN-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 andN-bromosuccinimide-promoted heteroarylations as well as standard oxidative and reductive conversions of the initially obtained adducts.