Umpolung Amination: Nickel-Catalyzed Coupling Reactions of N,N-Dialkyl-N-chloroamines with Diorganozinc Reagents

被引:151
作者
Barker, Timothy J. [1 ]
Jarvo, Elizabeth R. [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
ELECTROPHILIC AMINATION; REDUCTIVE ELIMINATION; COPPER; REACTIVITY; HALIDES;
D O I
10.1021/ja907038b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N,N-Dialkyl-N-chloroamines are an effective source of electrophilic nitrogen for nickel-catalyzed coupling with diarylzinc reagents. A variety of N-chloroamines as well as organozinc reagents react smoothly under the reaction conditions. A one-pot procedure that circumvents the need to isolate the N-chloroamines is described.
引用
收藏
页码:15598 / +
页数:3
相关论文
共 32 条
[21]   Practical palladium catalysts for C-N and C-O bond formation [J].
Muci, AR ;
Buchwald, SL .
CROSS-COUPLING REACTIONS: A PRACTICAL GUIDE, 2002, 219 :131-209
[22]   A general amination method based on the addition of polyfunctional arylmagnesium reagents to functionalized arylazo tosylates [J].
Sapountzis, I ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) :897-900
[23]   Improved reagent for electrophilic amination of stabilized carbanions [J].
Smulik, JA ;
Vedejs, E .
ORGANIC LETTERS, 2003, 5 (22) :4187-4190
[24]   TWIST CONFORMATION FOR THE CIS N,N-DIMETHYLPHOSPHORAMIDATE OF THYMIDINE 3',5'-CYCLIC PHOSPHATE [J].
SOPCHIK, AE ;
BENTRUDE, WG .
TETRAHEDRON LETTERS, 1980, 21 (49) :4679-4682
[25]   OXIDATIVE ADDITION OF BENZYL HALIDES TO TETRAKIS(TRIPHENYLPHOSPHINE)NICKEL(0) [J].
STILLE, JK ;
COWELL, AB .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 124 (02) :253-261
[26]   Nickel-on-charcoal-catalyzed aromatic aminations and Kumada couplings: Mechanistic and synthetic aspects [J].
Tasler, S ;
Lipshutz, BH .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1190-1199
[27]  
Watson IDG, 2002, CURR OPIN DRUG DISC, V5, P906
[28]   REACTIONS OF ZEROVALENT COMPLEX NI[HP(C6H5)2]41 [J].
WESTON, CW ;
VERSTUYFT, AW ;
NELSON, JH .
INORGANIC CHEMISTRY, 1977, 16 (06) :1313-1317
[29]   Reactivity of Pd(II) complexes with electrophilic chlorinating reagents: Isolation of Pd(IV) products and observation of C-Cl bond-forming reductive elimination [J].
Whitfield, Salena R. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15142-+
[30]   Rational development of practical catalysts for aromatic carbon-nitrogen bond formation [J].
Wolfe, JP ;
Wagaw, S ;
Marcoux, JF ;
Buchwald, SL .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) :805-818