Convenient synthesis of alkylhydrazides by the cobalt-catalyzed hydrohydrazination reaction of olefins and azodicarboxylates

被引：173

作者：

Waser, J ^{[1
]}

Carreira, EM ^{[1
]}

机构：

[1] ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 18期

关键词：

D O I：

10.1021/ja048698u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of olefins 2 with 1.5 equiv of di-tert-butyl azodicarboxylate (3), 1 equiv of PhSiH3, and 1.5-5 mol % of the simple Co(III) catalyst 1 in ethanol at 23 °C affords the Markovnikov hydrazide product for a broad range of olefins in 62-94% yield. Copyright © 2003 American Chemical Society.

引用

页码：5676 / 5677

页数：2

共 21 条

[1] The first method for protection-deprotection of the indole 2,3-π bond [J].

Baran, PS ;

Guerrero, CA ;

Corey, EJ .

ORGANIC LETTERS, 2003, 5 (11) :1999-2001

[2] ALLYLIC AMINATION BY THE LEWIS-ACID-MEDIATED ENE REACTION OF DIETHYL AZODICARBOXYLATE WITH ALKENES [J].

BRIMBLE, MA ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5261-5263

[3]

Brow B. R., 1994, ORGANIC CHEM ALIPHAT

[4] IRON(3) AND COBALT(3) COMPLEXES OF SOME N-SALICYLIDENEAMINO ACIDS [J].

BURROWS, RC ;

BAILAR, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (18) :4150-&

[5] THE STEREOCHEMISTRY OF FORWARD AND REVERSE REACTIONS IN THE ADDITION OF HYDRIDOCOBALOXIME TO (E)-1-PHENYLPROPENE [J].

DERENNE, S ;

GAUDEMER, A ;

JOHNSON, MD .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 322 (02) :229-238

[6] STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-HYDRAZINO AND ALPHA-AMINO-ACID DERIVATIVES [J].

EVANS, DA ;

BRITTON, TC ;

DOROW, RL ;

DELLARIA, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6395-6397

[7] Chiral magnesium bis(sulfonamide) complexes as catalysts for the merged enolization and enantioselective amination of N-acyloxazolidinones. A catalytic approach to the synthesis of arylglycines [J].

Evans, DA ;

Nelson, SG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (27) :6452-6453

[8] A NEW METHOD FOR PREPARATION OF ALCOHOLS FROM OLEFINS WITH MOLECULAR-OXYGEN AND PHENYLSILANE BY THE USE OF BIS(ACETYLACETONATO)COBALT(II) [J].

ISAYAMA, S ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1989, (06) :1071-1074

[9] AN EFFICIENT METHOD FOR THE DIRECT PEROXYGENATION OF VARIOUS OLEFINIC COMPOUNDS WITH MOLECULAR-OXYGEN AND TRIETHYLSILANE CATALYZED BY A COBALT(II) COMPLEX [J].

ISAYAMA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (05) :1305-1310

[10] NOVEL METHOD FOR THE PREPARATION OF TRIETHYLSILYL PEROXIDES FROM OLEFINS BY THE REACTION WITH MOLECULAR-OXYGEN AND TRIETHYLSILANE CATALYZED BY BIS(1,3-DIKETONATO)COBALT(II) [J].

ISAYAMA, S ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1989, (04) :573-576

← 1 2 3 →