Thermal 1,3-proton shift reaction and its application for operationally convenient and improved synthesis of α-(trifluoromethyl)benzylamine

被引：23

作者：

Yasumoto, Manabu ^{[1
]}

Ueki, Hisanori ^{[1
]}

Soloshonok, Vadim A. ^{[1
]}

机构：

[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2007年 / 128卷 / 07期

关键词：

thermal 1,3-proton shift reaction; fluorine compounds; imines; operationally convenient conditions; biomimetic reductive methodology;

D O I：

10.1016/j.jfluchem.2007.02.008

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

This paper describes a synthesis of alpha-(trifluoromethyl)benzylamine via a novel base-free biomimetic reductive amination of alpha,alpha,alpha-trifluoroacetophenone with benzylamine. When the corresponding imine, derived from alpha,alpha,alpha-trifluoroacetophenone and benzylamine was heated at 200 degrees C under N-2 for I day, the thermal 1,3-proton shift reaction took place giving rise to the N-(benzylidene)-alpha-(trifluoromethyl)benzylamine in quantitative yield. This thermal 1,3-proton shift reaction was used a key step in the development of new and substantially simplified, practical and operationally convenient procedure for preparation of the target alpha-(trifluoromethyl)benzylamine on large scale. (c) 2007 Elsevier B.V. All rights reserved.

引用

页码：736 / 739

页数：4

共 26 条

[1] Synthesis of highly 1,3-proton shift transferable N-benzyl imines of trifluoroacetophenone under the "low-basicity" reaction conditions [J].

Berbasov, DO ;

Ojemaye, ID ;

Soloshonok, VA .

JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (04) :603-607

[2] EIN BEITRAG ZUM STUDIUM DES REAKTIONSMECHANISMUS DER BIOLOGISCHEN TRANSAMINIERUNG [J].

BRANDENBERGER, H ;

COHEN, PP .

HELVETICA CHIMICA ACTA, 1953, 36 (03) :549-554

[3] Special issue - Current frontiers of fluoroorganic chemistry and recent advances in fluorous chemistry - Preface [J].

Curran, Dennis P. ;

Mikami, Koichi ;

Soloshonok, Vadim A. .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (4-5) :454-455

[4]

Fustero S, 2005, ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS, 2ND EDITION, P319, DOI 10.1002/0471698482.ch14

[5] ELECTROPHILIC SUBSTITUTION AT SATURATED CARBON .52. MODEL FOR THE PROTON-TRANSFER STEPS OF BIOLOGICAL TRANSAMINATION AND THE EFFECT OF A 4-PYRIDYL GROUP ON THE BASE-CATALYZED RACEMIZATION OF A CARBON ACID [J].

JAEGER, DA ;

BROADHURST, MD ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (03) :717-732

[6]

Juaristi E, 2005, ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS, 2ND EDITION, P1, DOI 10.1002/0471698482

[7]

KHOTKEVICH AB, 1990, ZH OBSHCH KHIM+, V60, P1005

[8]

KUKHAR VP, 1994, FLUORINE CONTAINING, V5, P221

[9] CHEMISTRY OF IMINES [J].

LAYER, RW .

CHEMICAL REVIEWS, 1963, 63 (05) :489-+

[10] VITAMIN-B6 CATALYZED-REACTIONS OF ALPHA-AMINO AND ALPHA-KETO ACIDS - MODEL SYSTEMS [J].

MARTELL, AE .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (04) :115-124

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