Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol

被引：140

作者：

Campbell, Matthew J. ^{[1
]}

Johnson, Jeffrey S. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 08期

关键词：

D O I：

10.1021/ol0702829

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An S(N)2 mechanism for the copper-catalyzed amination of diorganozinc reagents by O-benzoyl-N,N-dialkylhydroxylamines is supported by following stereochemically defined organometallics through the reaction and by employing the endocyclic restriction test. A copper-catalyzed electrophilic amination of organomagnesium compounds is also described in which the use of zinc halides has been eliminated.

引用

页码：1521 / 1524

页数：4

共 45 条

[1] PYRAMIDAL BONDING ABOUT NITROGEN IN 1-BENZOYLOXYINDOLE DETERMINED BY X-RAY-DIFFRACTION [J].

ACHESON, RM ;

BENN, MH ;

JACYNO, J ;

WALLIS, JD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (04) :497-500

[2]

ARMSTRONG DR, 1985, CHEM COMMUN, P789

[3] Alkylation of aromatic amines and related compounds using a copper(II)-aluminum(II) couple [J].

Barton, DHR ;

Doris, E .

TETRAHEDRON LETTERS, 1996, 37 (19) :3295-3298

[4] DETERMINATIONS OF TRANSITION-STATE GEOMETRIES BY THE ENDOCYCLIC RESTRICTION TEST - MECHANISMS OF SUBSTITUTION AT NONSTEREOGENIC ATOMS [J].

BEAK, P .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (05) :215-222

[5] THE GEOMETRY OF DISPLACEMENTS AT NONSTEREOGENIC ATOMS - THE FORMAL DISPLACEMENT OF ALKOXIDE FROM ALKOXYAMINES BY ORGANOLITHIUM REAGENTS [J].

BEAK, P ;

BASHA, A ;

KOKKO, B ;

LOO, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6016-6023

[6] DISPLACEMENTS AT THE NITROGEN OF LITHIOALKOXYLAMIDES BY ORGANOMETALLIC REAGENTS [J].

BEAK, P ;

SELLING, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23) :5574-5580

[7] THE ENDOCYCLIC RESTRICTION TEST - EXPERIMENTAL EVALUATION OF TRANSITION-STRUCTURE GEOMETRY FOR A NUCLEOPHILIC DISPLACEMENT AT NEUTRAL NITROGEN [J].

BEAK, P ;

LI, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2796-2797

[8] Copper-catalyzed electrophilic amination of organozinc nucleophiles:: Documentation of O-benzoyl hydroxylamines as broadly useful R2N(+) and RHN(+) synthons [J].

Berman, AM ;

Johnson, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :219-224

[9] Copper-catalyzed electrophilic amination of functionalized diarylzinc reagents [J].

Berman, AM ;

Johnson, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :364-366

[10] Copper-catalyzed electrophilic amination of diorganozinc reagents [J].

Berman, AM ;

Johnson, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5680-5681

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