Preparation of Substituted Tetrahydroisoquinolines by Pd(II)-Catalyzed NH2-Directed Insertion of Michael Acceptors into C-H Bonds Followed by NH2-Conjugated Addition

被引：21

作者：

Mancinelli, Andrea ^{[1
,2
]}

Alamillo, Carla ^{[1
,2
]}

Albert, Joan ^{[1
]}

Ariza, Xavier ^{[1
,2
,3
]}

Etxabe, Haizea ^{[1
,2
]}

Farras, Jaume ^{[1
,2
]}

Garcia, Jordi ^{[1
,2
,3
]}

Granell, Jaume ^{[1
]}

Quijada, F. Javier ^{[1
,2
]}

机构：

[1] Univ Barcelona, Fac Quim, Secc Quim Organ, Dept Quim Inorgan & Organ, Marti Franques 1-11, Barcelona 08028, Spain

[2] Univ Barcelona, Fac Quim, Inst Biomed IBUB, Marti Franques 1-11, Barcelona 08028, Spain

[3] Inst Salud Carlos III, CIBER Fisiopatol Obesidad & Nutr CIBERob, Madrid 28029, Spain

来源：

ORGANOMETALLICS | 2017年 / 36卷 / 04期

关键词：

FREE AMINO GROUP; DIRECTING GROUP; PALLADIUM CATALYSIS; ORTHO-ARYLATION; ACTIVATION; ALKENYLATION; BENZYLAMINES; FUNCTIONALIZATIONS; DERIVATIVES; C(SP(2))-H;

D O I：

10.1021/acs.organomet.6b00944

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

3,3-Disubstituted tetrahydroisoquinolines are prepared in one step from Michael acceptors and 2-phenylethylamines under Pd catalysis and Ag2CO3 as an oxidant. Presumably, activation of an ortho C-H bond of the aromatic ring with Pd(II) is directed by the primary amine to form a palladacycle. Insertion of the olefin, subsequent conjugated addition of the amine, and reductive elimination of Pd(0) affords the expected products. Silver carbonate is not necessary when 2-phenylethylamines are converted previously to N-benzoyloxy-2-phenylethylamines.

引用

页码：911 / 919

页数：9

共 55 条

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