Application of the Suzuki reaction as the key step in the synthesis of a novel atropisomeric biphenyl derivative for use as a liquid crystal dopant

被引：68

作者：

Cammidge, AN ^{[1
]}

Crépy, KVL ^{[1
]}

机构：

[1] Univ E Anglia, Sch Chem Sci & Pharm, Wolfson Mat & Catalysis Ctr, Norwich NR4 7TJ, Norfolk, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 17期

关键词：

D O I：

10.1021/jo034652s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A heavily functionalized atropisomeric biphenyl derivative (4), which is designed to possess a large lateral dipole moment, has been synthesized with use of a Suzuki coupling as the key step and resolved by chiral HPLC. The final coupling reaction is complicated by rapid hydrolytic deboronation of the sterically hindered, electron poor boronate 22. Rigorously anhydrous conditions are therefore necessary to achieve the coupling.

引用

收藏

页码：6832 / 6835

页数：4

相关论文

共 36 条

[1] PALLADIUM-CATALYZED REDUCTION OF ARYL SULFONATES - REDUCTION VERSUS HYDROLYSIS AND SELECTIVITY CONTROL [J].

CABRI, W ;

DEBERNARDINIS, S ;

FRANCALANCI, F ;

PENCO, S ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :350-353

[2] PALLADIUM-CATALYZED TRIETHYLAMMONIUM FORMATE REDUCTION OF ARYL TRIFLATES - A SELECTIVE METHOD FOR THE DEOXYGENATION OF PHENOLS [J].

CACCHI, S ;

CIATTINI, PG ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON LETTERS, 1986, 27 (45) :5541-5544

[3] The first asymmetric Suzuki cross-coupling reaction [J].

Cammidge, AN ;

Crépy, KVL .

CHEMICAL COMMUNICATIONS, 2000, (18) :1723-1724

[4] MECHANISM OF PRIMARY ALIPHATIC-AMINES OXIDATION TO NITRILES BY THE CUPROUS CHLORIDE-DIOXYGEN-PYRIDINE SYSTEM [J].

CAPDEVIELLE, P ;

LAVIGNE, A ;

SPARFEL, D ;

BARANNELAFONT, J ;

CUONG, NK ;

MAUMY, M .

TETRAHEDRON LETTERS, 1990, 31 (23) :3305-3308

[5]

CAPDEVIELLE P, 1989, SYNTHESIS-STUTTGART, P453

[6] Asymmetric Suzuki cross-coupling reaction: chirality reversal depending on the palladium-chiral phosphine ratio [J].

Castanet, AS ;

Colobert, F ;

Broutin, PE ;

Obringer, M .

TETRAHEDRON-ASYMMETRY, 2002, 13 (06) :659-665

[7]

Collings P. J., 1997, INTRO LIQUID CRYSTAL

[8] The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst [J].

Dai, CY ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2719-2724

[9]

Dewick P. M., 2002, MED NATURAL PRODUCTS

[10] Enediols. VIII. Methoxystilbenediols [J].

Fuson, RC ;

Corse, J ;

Welldon, PB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 :2645-2648

← 1 2 3 4 →