One-pot, solvent-free Pd(II)-catalyzed direct β-C-H arylation of carboxamides involving anhydrides as substrates via in situ installation of directing group

被引:9
作者
Dalal, Arup [1 ]
Singh, Prabhakar [1 ]
Babu, Srinivasarao Arulananda [1 ]
机构
[1] Indian Inst Sci Educ & Res USER Mohali, Dept Chem Sci, Sect 81,Manauli PO, Manauli 140306, Punjab, India
关键词
Carboxamides; C-H activation; Multicomponent reaction; Palladium; C-H arylation; UNACTIVATED C(SP(3))-H BONDS; CATALYZED ARYLATION; PALLADIUM(II)-CATALYZED ARYLATION; ALIPHATIC AMIDES; CARBOXYLIC-ACIDS; PALLADIUM; BIDENTATE; FUNCTIONALIZATION; ACTIVATION; AUXILIARY;
D O I
10.1016/j.tet.2019.01.042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot, multicomponent-type, solvent-free Pd(II)-catalyzed direct beta-C-H activation/arylation of carboxamides involving anhydrides as substrates via in situ installation of directing group (DG) is reported. Typically, the DG-assisted beta-C-H activation/arylation of carboxamides is a two-step process comprising the installation of DG and Pd(II)-catalyzed C-H arylation. We attempted a multicomponent-type reaction comprising an anhydride, a DG (e.g. 8-aminoquinoline), an aryl iodide in the presence of the Pd(II) catalyst and an appropriate additive. Different anhydrides, DGs, aryl iodides, catalysts and additives were screened to reveal the scope of this multicomponent-type C-H arylation reaction process and various beta-C-H arylated carboxamides were obtained in satisfactory to good yields. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1246 / 1257
页数:12
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