使用联芳基膦钯（0）配合物在室温下几乎瞬间实现的[（11）C]氰化反应。
Virtually instantaneous, room-temperature [(11)C]-cyanation using biaryl phosphine Pd(0) complexes.
作者信息
Lee Hong Geun, Milner Phillip J, Placzek Michael S, Buchwald Stephen L, Hooker Jacob M
机构信息
Massachusetts Institute of Technology , 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
出版信息
J Am Chem Soc. 2015 Jan 21;137(2):648-51. doi: 10.1021/ja512115s. Epub 2015 Jan 9.
Abstract
A new radiosynthetic protocol for the preparation of [(11)C]aryl nitriles has been developed. This process is based on the direct reaction of in situ prepared L·Pd(Ar)X complexes (L = biaryl phosphine) with [(11)C]HCN. The strategy is operationally simple, exhibits a remarkably wide substrate scope with short reaction times, and demonstrates superior reactivity compared to previously reported systems. With this procedure, a variety of [(11)C]nitrile-containing pharmaceuticals were prepared with high radiochemical efficiency.
摘要
已开发出一种用于制备[(11)C]芳基腈的新的放射性合成方案。该方法基于原位制备的L·Pd(Ar)X配合物（L = 联芳基膦）与[(11)C]HCN的直接反应。该策略操作简单，底物范围广，反应时间短，与先前报道的体系相比显示出优异的反应活性。通过该方法，以高放射化学效率制备了多种含[(11)C]腈的药物。
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Virtually instantaneous, room-temperature [(11)C]-cyanation using biaryl phosphine Pd(0) complexes.使用联芳基膦钯（0）配合物在室温下几乎瞬间实现的[（11）C]氰化反应。
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Inorganica Chim Acta. 2014 Oct 1;422:188-192. doi: 10.1016/j.ica.2014.06.008.
2
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3
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6
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7
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8
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10
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