Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes.

Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes.
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DOI:
10.1021/ja3116718
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发表时间:
2013-01-30
影响因子:
15
通讯作者:
Jamison, Timothy F.
Jamison, Timothy F.
中科院分区:
化学1区
文献类型:
--
作者:
Standley, Eric A.;Jamison, Timothy F.

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空气稳定的镍(II)配合物反式-(PCy2Ph)2Ni(邻甲苯基)Cl的合成和表征结合其用于Mizoroki Heck型,室温,内部选择性耦合取代的苄基氯与末端烯烃的调查。该反应采用末端烯烃作为烯基金属等价物,以高产率和在几乎所有情况下大于95:5的区域选择性提供了快速、收敛的获得取代的烯丙基苯衍生物的途径。该反应操作简单,可以在工作台上进行,无需纯化或脱气溶剂或试剂,并且在设置期间不需要排除空气或水。预催化剂的合成通过简单的程序完成,该程序采用廉价的市售试剂,不需要纯化步骤,并且以高产率进行。
The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy2Ph)2Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for Mizoroki Heck-type, room temperature, internally-selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the bench-top with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield.
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