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H–D exchange in deuterated trifluoroacetic acid via ligand-directed NHC–palladium catalysis: a powerful method for deuteration of aromatic ketones, amides, and amino acids
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2015-10-14 15:53:27 Richard Giles, Green Ahn, Kyung Woon Jung
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2015-10-14 15:53:27 Richard Giles, Green Ahn, Kyung Woon Jung
A method has been developed for one-step ortho-selective ligand-directed H–D exchange, accompanied in some cases by concurrent acid-catalyzed electrophilic deuteration. This method is effective for deuteration of aromatic substrates ranging from ketones to amides and amino acids, including compounds of biological and pharmaceutical interest such as acetaminophen and edaravone. Use of a palladium catalyst featuring an NHC ligand is critical for the observed reactivity. Experimental evidence strongly suggests that palladium facilitates C–H activation of the aromatic substrates, a mechanism seldom observed under strongly acidic conditions.
中文翻译:
通过配体导向的NHC-钯催化在氘代三氟乙酸中进行H–D交换:一种强大的使芳族酮,酰胺和氨基酸氘化的方法
已经开发出一种方法,用于一步一步的邻位选择性配体导向的H–D交换,在某些情况下还伴有酸催化的亲电氘代反应。该方法对于氘化从酮到酰胺和氨基酸的芳香族底物,包括对乙酰氨基酚和依达拉奉等具有生物学和药学意义的化合物是有效的。使用具有NHC配体的钯催化剂对于观察到的反应性至关重要。实验证据强烈表明,钯促进了芳香族底物的C–H活化,这在强酸性条件下很少观察到。
更新日期:2015-10-15
中文翻译:
通过配体导向的NHC-钯催化在氘代三氟乙酸中进行H–D交换:一种强大的使芳族酮,酰胺和氨基酸氘化的方法
已经开发出一种方法,用于一步一步的邻位选择性配体导向的H–D交换,在某些情况下还伴有酸催化的亲电氘代反应。该方法对于氘化从酮到酰胺和氨基酸的芳香族底物,包括对乙酰氨基酚和依达拉奉等具有生物学和药学意义的化合物是有效的。使用具有NHC配体的钯催化剂对于观察到的反应性至关重要。实验证据强烈表明,钯促进了芳香族底物的C–H活化,这在强酸性条件下很少观察到。