Catalytic ester-amide exchange using group (IV) metal alkoxide-activator complexes

被引:157
作者
Han, C
Lee, JP
Lobkovsky, E
Porco, JA [1 ]
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Ctr Chem Methodol & Lib Dev, Boston, MA 02215 USA
[3] Cornell Univ, Baker Lab, Dept Chem, Ithaca, NY 14583 USA
关键词
D O I
10.1021/ja0527976
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A process for preparation of amides from unactivated esters and amines has been developed using a catalytic system comprised of group (IV) metal alkoxides in conjunction with additives including 1-hydroxy-7-azabenzotriazole (HOAt). In general, ester-amide exchange proceeds using a variety of structurally diverse esters and amines without azeotropic reflux to remove the alcohol byproduct. Initial mechanistic studies on the Zr(Ot-Bu)(4)-HOAt system revealed that the active catalyst is a novel, dimeric zirconium complex as determined by X-ray crystallography.
引用
收藏
页码:10039 / 10044
页数:6
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共 70 条
[51]   Efficient method for preparation of N-methoxy-N-methyl amides by reaction of lactones or esters with Me(2)AlCl-MeONHMe center dot HCl [J].
Shimizu, T ;
Osako, K ;
Nakata, T .
TETRAHEDRON LETTERS, 1997, 38 (15) :2685-2688
[52]   SYNTHESIS OF 7,9-DIDECARBOXYMETHOXATIN (4,5-DIHYDRO-4,5-DIOXO-1H-PYRROLO[2,3-F]QUINOLINE-2-CARBOXYLIC ACID) AND COMPARISON OF ITS CHEMICAL-PROPERTIES WITH THOSE OF METHOXATIN AND ANALOGOUS ORTHO-QUINONES - MODEL STUDIES DIRECTED TOWARD THE ACTION OF PQQ REQUIRING BACTERIAL OXIDOREDUCTASES AND MAMMALIAN PLASMA AMINE OXIDASEH [J].
SLEATH, PR ;
NOAR, JB ;
EBERLEIN, GA ;
BRUICE, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (11) :3328-3338
[53]   THE CRYSTAL-STRUCTURE OF DI-MU-CHLOROBIS[TRICHLORO(ETHYL ACETATE)]DIZIRCONIUM(IV) [J].
SOBOTA, P ;
MUSTAFA, MO ;
LIS, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 377 (01) :69-74
[54]   A highly convenient, efficient, and selective process for preparation of esters and amides from carboxylic acids using Fe3+-K-10 montmorillonite clay [J].
Srinivas, KVNS ;
Das, B .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :1165-1167
[55]   Zirconium(IV) chloride catalyzed ring opening of epoxides with aromatic amines [J].
Swamy, NR ;
Goud, TV ;
Reddy, SM ;
Krishnaiah, P ;
Venkateswarlu, Y .
SYNTHETIC COMMUNICATIONS, 2004, 34 (04) :727-734
[56]   Metallo-esterification of alkynes:: Reaction of alkynes with Cp2ZrEt2 and chloroformate [J].
Takahashi, T ;
Xi, CJ ;
Ura, Y ;
Nakajima, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) :3228-3229
[57]   Ferromagnetism in an extended three-dimensional, diamond-like copper(II) network: A new copper(II)/1-hydroxybenzotriazolato complex exhibiting soft-magnet properties and two transitions at 6.4 and 4.4 K [J].
Tangoulis, V ;
Raptopoulou, CP ;
Psycharis, V ;
Terzis, A ;
Skorda, K ;
Perlepes, SP ;
Cador, O ;
Kahn, O ;
Bakalbassis, EG .
INORGANIC CHEMISTRY, 2000, 39 (12) :2522-2529
[58]   A family of group 4 metal alkoxo complexes with an M3(μ3-O) core relevant to Ziegler-Natta catalyst intermediates [J].
Utko, J ;
Przybylak, S ;
Jerzykiewicz, LB ;
Szafert, S ;
Sobota, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (01) :181-190
[59]   Cu(OBt)2 and Cu(OAt)2, copper(II)-based racemization suppressors ready for use in fully automated solid-phase peptide synthesis [J].
Van den Nest, W ;
Yuval, S ;
Albericio, F .
JOURNAL OF PEPTIDE SCIENCE, 2001, 7 (03) :115-120
[60]   Solvent-free synthesis of amides from non-enolizable eaters and amines using microwave irradiation [J].
Varma, RS ;
Naicker, KP .
TETRAHEDRON LETTERS, 1999, 40 (34) :6177-6180