Oxidative α-Functionalization of 1,2,3,4-Tetrahydroisoquinolines Catalyzed by a Magnetically Recoverable Copper Nanocatalyst. Application in the Aza-Henry Reaction and the Synthesis of 3,4-Dihydroisoquinolones

被引：17

作者：

Bjerg, Esteban E. ^{[1
]}

Marchan-Garcia, Joaquin ^{[1
]}

Buxaderas, Eduardo ^{[1
]}

Moglie, Yanina ^{[1
]}

Radivoy, Gabriel ^{[1
]}

机构：

[1] Univ Nacl Sur, Inst Quim Sur, Dept Quim, INQUISUR CONICET UNS, RA-8000 Bahia Blanca, Buenos Aires, Argentina

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 20期

关键词：

DEHYDROGENATIVE COUPLING REACTIONS; C-H FUNCTIONALIZATION; SUPPORTED GOLD NANOPARTICLES; AEROBIC OXIDATION; TERTIARY-AMINES; BIOLOGICAL EVALUATION; ASYMMETRIC-SYNTHESIS; EFFICIENT CATALYST; BENZYLIC AMINES; CYCLIC AMINES;

D O I：

10.1021/acs.joc.2c01782

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidative alpha-functionalization of 2-aryl-1,2,3,4tetrahydroisoquinolines (THIQs) promoted by a versatile heterogeneous nanocatalyst consisting of copper nanoparticles immobilized on silica-coated maghemite (CuNPs/MagSilica) has been accomplished. The methodology was successfully applied in the cross-dehydrogenative coupling (CDC) reaction of N-aryl THIQs and other tertiary amines with nitromethane as a pronucleophile (aza-Henry reaction) and the alpha-oxidation of THIQs with O2 as a green oxidant. Phosphite, alkyne, or indole derivatives were also shown to be suitable candidates for their use as pro-nucleophiles in the CDC reaction with THIQs. The catalyst, with very low copper loading (0.4-1.0 mol % Cu), could be easily recovered by means of an external magnet and reused in four cycles without significant loss of activity.

引用

页码：13480 / 13493

页数：14

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