Base-Catalyzed Halogen Dance Reaction and Oxidative Coupling Sequence as a Convenient Method for the Preparation of Dihalo-bisheteroarenes

被引：53

作者：

Getmanenko, Yulia A. ^{[1
,2
]}

Tongwa, Paul ^{[3
]}

Timofeeva, Tatiana V. ^{[3
]}

Marder, Seth R. ^{[1
,2
]}

机构：

[1] Georgia Inst Technol, Dept Chem & Biochem, Atlanta, GA 30332 USA

[2] Georgia Inst Technol, Ctr Organ Photon & Elect, Atlanta, GA 30332 USA

[3] New Mexico Highlands Univ, Dept Chem, Las Vegas, NM 87701 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 09期

基金：

美国国家科学基金会;

关键词：

FIELD-EFFECT TRANSISTORS; POLYMERS; MOBILITY; COPOLYMERS;

D O I：

10.1021/ol1006423

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot preparation of the 2,2'-dibromo-1,1'-bisheteroarenes 3a-d from bromo-heteroarenes utilizing the sequence of the base-catalyzed halogen dance (BCHD) reaction and CuCl(2)-promoted oxidative coupling of the in situ formed alpha-lithio-beta-halo-heteroarenes 2a-d provides a convenient access to precursors for the preparation of tricyclic heteroaromatic cores. The structures of 3a,b,d, 6, and 9 were confirmed by single-crystal X-ray analysis, and dibromides 3a and 3b were used for the preparation of dithieno-[2,3-b:3',2'-d]-pyrrole 10a and its selenophene analogue 10b, respectively.

引用

页码：2136 / 2139

页数：4

共 7 条

[1] New preparation method for halogenated ethanes and methanes via base-catalyzed halogen dance
FU
Chinese Journal of Chemistry, 1992, (02) : 189 - 192
[2] A base-catalyzed domino reaction between isoindigos and α-alkylidene succinimides-convenient preparation of highly steric bispirooxindoles
Li, Chen-Yi
Xiang, Min
Song, Xiang-Jia
Zou, Ying
Huang, Zhi-Cheng
Li, Xia
Tian, Fang
Wang, Li-Xin
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (46) : 9511 - 9515
[3] BASE-CATALYZED HALOGEN DANCE REACTION AT THIOPHENES - A SPECTROSCOPIC REINVESTIGATION OF THE SYNTHESIS OF 2,5-DIBROMO-3-(TRIMETHYLSILYL)THIOPHENE
FROHLICH, H
KALT, W
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10): : 2993 - 2995
[4] SYNTHESIS OF 2-SUBSTITUTED 3,5-DIBROMOTHIOPHENES VIA A REARRANGEMENT REACTION - A NEW EXAMPLE OF A BASE-CATALYZED HALOGEN DANCE REACTION
SAUTER, F
FROHLICH, H
KALT, W
SYNTHESIS-STUTTGART, 1989, (10): : 771 - 773
[5] BASE-CATALYZED OXYGENATION OF 2,6-DI-TERT-BUTYLPHENOLS - CONVENIENT METHOD FOR PREPARATION OF PARA-QUINOLS
NISHINAGA, A
ITAHARA, T
MATSUURA, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1975, 48 (05) : 1683 - 1683
[6] SYNTHESIS OF 2-SUBSTITUTED 3,5-DIBROMOTHIOPHENES THROUGH BASE-CATALYZED HALOGEN DANCE REACTION OF 2,5-DIBROMOTHIOPHENE
KANO, S
YUASA, Y
YOKOMATSU, T
SHIBUYA, S
HETEROCYCLES, 1983, 20 (10) : 2035 - 2037
[7] Triphenylphosphine-catalyzed dehydrogenative coupling reaction of carboxylic acids with silanes - A convenient method for the preparation of silyl esters
Liu, Guo-Bin
Zhao, Hong-Yun
Thiemann, Thies
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (06) : 807 - 811

← 1 →