A General Method for Two-Step Transamidation of Secondary Amides Using Commercially Available, Air- and Moisture-Stable Palladium/NHC (N-Heterocyclic Carbene) Complexes

A General Method for Two-Step Transamidation of Secondary Amides Using Commercially Available, Air- and Moisture-Stable Palladium/NHC (N-Heterocyclic Carbene) Complexes
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DOI:
10.1021/acs.orglett.7b00796
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发表时间:
2017-04-21
期刊:
影响因子:
5.2
通讯作者:
Szostalek, Michal
Szostalek, Michal
中科院分区:
化学1区
文献类型:
--
作者:
Meng, Guangrong;Lei, Peng;Szostalek, Michal

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第一个通用的方法,报道了由Pd-NHC(NHC = N-杂环卡宾)配合物催化的仲酰胺基转移。市售的空气和水分稳定的(NHC)Pd(R-ally)Cl络合物可以实现广泛的N-Boc和N-Ts酰胺的C-N交叉偶联,以非常好的产率获得选择性酰胺N-官能化,与非亲嗜中性苯胺和空间位阻胺。首次将多功能钯-NHC络合物作为催化剂用于过渡金属催化的酰胺的N-C活化的C(酰基)N胺化反应。
The first general method is reported for transamidation of secondary,carboxamides catalyzed by Pd-NHC (NHC = N-heterocyclic carbene) complexes. Commercially available, air- and moisture-stable (NHC)Pd(R-ally1)Cl complexes can effect C-N cross-coupling of a wide range of N-Boc and N-Ts amides, obtained selective amide N-functionaliiation, with non-hudeophilic anilines and stetically hindered amines in very good yields. The first use of versatile Pd-NHC complexes as catalysts is represented for transition metal -catalyzed C(acyl) N amination of amides by N C activation.