Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts.

Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts.
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DOI:
10.1021/ol401612c
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发表时间:
2013-07-19
期刊:
影响因子:
5.2
通讯作者:
Buchwald, Stephen L.
Buchwald, Stephen L.
中科院分区:
化学1区
文献类型:
--
作者:
Cheung, Chi Wai;Surry, David S.;Buchwald, Stephen L.

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本发明描述了一种钯催化的氨与广泛的芳基和杂芳基卤化物(包括具有挑战性的五元杂环底物)的芳基化的方法。通过使用大体积联芳基膦配体(L6、L7和L4)以及它们相应的氨基联苯钯预催化剂(3a、3b和3c),在温和条件下或在室温下实现了氨单芳基化为伯芳基胺的优异选择性。由于这种方法既不需要使用手套箱,也不需要高压氨,因此应该广泛适用。
A method for the palladium-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at room temperature by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.
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