Understanding the behavior of N-tosyl and N-2-pyridylsulfonyl Imines in CuII-Catalyzed aza-friedel-crafts reactions

被引：64

作者：

Alonso, Ines ^{[1
]}

Esquivias, Jorge ^{[1
]}

Gomez-Arrayas, Ramon ^{[1
]}

Carretero, Juan C. ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, Fac Ciencias, E-28049 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 16期

关键词：

D O I：

10.1021/jo800986g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The different behavior of N-tosyl imines and N-(2-pyridyl)sulfonyl imines in Cu-II-catalyzed AFCR is described. DFT theoretical calculations on the mode of coordination of the copper atom to both types of substrates allow understanding this different reactivity.

引用

页码：6401 / 6404

页数：4

共 39 条

[1] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].

Bandini, M ;

Melloni, A ;

Umani-Ronchi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556

[2] A NEW MIXING OF HARTREE-FOCK AND LOCAL DENSITY-FUNCTIONAL THEORIES [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (02) :1372-1377

[3] Organocatalytic synthesis of dipyrromethanes by the addition of N-methylpyrrole to aldehydes [J].

Biaggi, Cinzia ;

Benaglia, Maurizio ;

Raimondi, Laura ;

Cozzi, Franco .

TETRAHEDRON, 2006, 62 (52) :12375-12379

[4] SELF-CONSISTENT MOLECULAR-ORBITAL METHODS .9. EXTENDED GAUSSIAN-TYPE BASIS FOR MOLECULAR-ORBITAL STUDIES OF ORGANIC MOLECULES [J].

DITCHFIELD, R ;

HEHRE, WJ ;

POPLE, JA .

JOURNAL OF CHEMICAL PHYSICS, 1971, 54 (02) :724-+

[5] A copper(II)-catalyzed aza-Friedel-Crafts reaction of N-(2-pyridyl)sulfonyl aldimines:: Synthesis of unsymmetrical diaryl amines and triaryl methanes [J].

Esquivias, J ;

Arrayás, RG ;

Carretero, JC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (04) :629-633

[6] Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to (2-pyridyl)sulfonyl imines of chalcones [J].

Esquivias, J ;

Arrayás, RG ;

Carretero, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (18) :7451-7454

[7] Alkylation of aryl N-(2-pyridylsulfonyl)aldimines with organozinc halides:: Conciliation of reactivity and chemoselectivity [J].

Esquivias, Jorge ;

Gomez Arrayas, Ramon ;

Carlos Carretero, Juan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9257-9260

[8]

Frisch M. J., 2016, J AM CHEM SOC, DOI DOI 10.1021/JA205566W

[9]

Gong Y, 2000, SYNLETT, P1058

[10] Diastereoselective Friedel-Crafts reaction of α-trifluoromethyl imines derived from chiral amines [J].

Gong, YF ;

Kato, K .

TETRAHEDRON-ASYMMETRY, 2001, 12 (15) :2121-2127

← 1 2 3 4 →