Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts:: 2-N,N-diisopropylaminophenylboronate derivatives

被引：58

作者：

Coghlan, SW

Giles, RL

Howard, JAK

Patrick, LGF

Probert, MR

Smith, GE

Whiting, A ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3LE, England

[2] GlaxoSmithKline Res & Dev Ltd, Nr Tonbridge TN11 9AN, Kent, England

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2005年 / 690卷 / 21-22期

基金：

英国工程与自然科学研究理事会;

关键词：

metallation; arylamine; arylboronate; boronic acid; aryldifluoroborane; NMR; X-ray;

D O I：

10.1016/j.jorganchem.2005.07.108

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Directed ortho-metallation is used to introduce a boron function into N,N-diisopropylbenzamide,. resulting in the formation of both borinate and boronate derivatives. N,N-Diisopropylbenzamide ortho-boronate pinacol ester can be reduced with sodium borohydride-TMSCl resulting in N,N-diisopropylbenzylamino ortho-boronic acid. X-ray crystallography and B-11 NMR of this compound clearly shows that the hindered isopropylamino groups are sufficient to prevent B-N intramolecular coordination, which contrasts with NN-dimethylbenzylamino ortho-boronic acid. (c) 2005 Elsevier B.V. All rights reserved.

引用

收藏

页码：4784 / 4793

页数：10

相关论文

共 26 条

[1] THE TERTIARY AMIDE AS AN EFFECTIVE DIRECTOR OF ORTHO LITHIATION [J].

BEAK, P ;

BROWN, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) :34-46

[2]

*CAMBR CRYST DAT C, 2005, CAMBR STRUCT DAT

[3] Application of arylboron difluoride Lewis acid catalysts to the Diels-Alder reaction: Convenient, non-volatile alternatives to boron trifluoride. [J].

de la Torre, MF ;

Caballero, MC ;

Whiting, A .

TETRAHEDRON, 1999, 55 (28) :8547-8554

[4] ORTHO AND REMOTE METALATION CROSS-COUPLING STRATEGIES - TOTAL SYNTHESIS OF THE NATURALLY-OCCURRING FLUORENONE DENGIBSININ AND THE AZAFLUORANTHENE ALKALOID IMELUTEINE [J].

FU, JM ;

ZHAO, BP ;

SHARP, MJ ;

SNIECKUS, V .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (01) :227-236

[5] LIBH4(NABH4) ME3SICL, AN UNUSUALLY STRONG AND VERSATILE REDUCING AGENT [J].

GIANNIS, A ;

SANDHOFF, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (02) :218-220

[6] Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts:: 1-N,N-dimethylamino-8-borononaphthalene derivatives [J].

Giles, RL ;

Howard, JAK ;

Patrick, LGF ;

Probert, MR ;

Smith, GE ;

Whiting, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 680 (1-2) :257-262

[7] Boronic acid receptors for α-hydroxycarboxylates:: High affinity of Shinkai's glucose receptor for tartrate [J].

Gray, CW ;

Houston, TA .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5426-5428

[8] Allylation of ketones with allylstannanes catalyzed by Lewis acid-Lewis base combined reagents [J].

Hamasaki, R ;

Chounan, Y ;

Horino, H ;

Yamamoto, Y .

TETRAHEDRON LETTERS, 2000, 41 (50) :9883-9887

[9] Highly enantioselective cyanosilylation of aldehydes catalyzed by a Lewis acid-Lewis base bifunctional catalyst [J].

Hamashima, Y ;

Sawada, D ;

Nogami, H ;

Kanai, M ;

Shibasaki, M .

TETRAHEDRON, 2001, 57 (05) :805-814

[10] Catalytic enantioselective cyanosilylation of ketones: improvement of enantioselectivity and catalyst turn-over by ligand tuning [J].

Hamashima, Y ;

Kanai, M ;

Shibasaki, M .

TETRAHEDRON LETTERS, 2001, 42 (04) :691-694