3,4-DISUBSTITUTED FURANS .4. REGIOSPECIFIC CONVERSION OF 3,4-BIS(TRIMETHYLSILYL)FURAN TO 3,4-DISUBSTITUTED FURANS - A NOVEL SUZUKI-TYPE CROSS-COUPLING OF BOROXINES

被引：32
|
作者：
SONG, ZZ
ZHOU, ZY
MAK, TCW
WONG, HNC
机构：
[1] CHINESE UNIV HONG KONG,DEPT CHEM,SHA TIN,HONG KONG
[2] LANZHOU UNIV,LANZHOU,PEOPLES R CHINA
[3] CHINESE ACAD SCI,CTR ANAL & TESTING,CHENGDU,PEOPLES R CHINA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 03期
关键词：
D O I：
10.1002/anie.199304321
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A versatile building block is found in the easily s(trimethylsilyl)furan, which can be converted into boroxine 1 with BCl3 followed by aqueous workup. Subsequent Pd-catalyzed treatment with organic halides furnishes monoorganosilylfuran. Repetition of this reaction sequence affords 3,4-disubstituted furans, which are difficult to obtain by other methods. [GRAPHICS]
引用
收藏
页码：432 / 434
页数：3
相关论文
共 50 条
  • [31] Synthesis of 2-(Substituted Methyl)-3,4-disubstituted pyrroles and their conversion into the corresponding porphyrins
    Kinoshita, Hideki
    Tanaka, Shingo
    Nishimori, Natsu
    Dejima, Hiroshi
    Inomata, Katsuhiko
    Bulletin of the Chemical Society of Japan, 1992, 65 (10): : 2660 - 2667
  • [32] SYNTHESIS OF 2-(SUBSTITUTED METHYL)-3,4-DISUBSTITUTED PYRROLES AND THEIR CONVERSION INTO THE CORRESPONDING PORPHYRINS
    KINOSHITA, H
    TANAKA, S
    NISHIMORI, N
    DEJIMA, H
    INOMATA, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (10) : 2660 - 2667
  • [33] Kinetic Resolution of Racemic 3,4-Disubstituted 1,4,5,6-Tetrahydropyridine and 3,4-Disubstituted 1,4-Dihydropyridines via Rh-Catalyzed Asymmetric Hydrogenation
    Li, Wendian
    Yang, Hailong
    Li, Ruihao
    Lv, Hui
    Zhang, Xumu
    ACS CATALYSIS, 2020, 10 (04) : 2603 - 2608
  • [34] REGIOSPECIFIC DISPLACEMENT OF THE C-B BOND OF TRIS[4-(SUBSTITUTED)FURAN-3-YL]BOROXINES WITH C-SN BOND AND C-O BOND - SYNTHESES OF 3,4-DISUBSTITUTED FURANS AND 4-SUBSTITUTED-3(2H)-FURANONES
    SONG, ZZ
    WONG, HNC
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1995, 42 (04) : 673 - 679
  • [35] Reactions of tetracyclic γ-sultones with N-nucleophiles. Novel synthesis of 3,4-disubstituted homoadamantanes
    Baimuratov, Marat R.
    Leonova, Marina V.
    Shiryaev, Vadim A.
    Klimochkin, Yuri N.
    TETRAHEDRON, 2017, 73 (43) : 6101 - 6108
  • [36] Design and synthesis of novel 3,4-disubstituted pyrazoles for nanomedicine applications against malignant gliomas
    Franchini, Mauro Comes
    Bonini, Bianca Flavia
    Camaggi, Carlo Maurizio
    Gentili, Denis
    Pession, Annalisa
    Rani, Monica
    Strocchi, Elena
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (05) : 2024 - 2033
  • [37] A NOVEL FORMATION OF 3,4-DISUBSTITUTED ISOTHIAZOLES FROM 5-AMINO-6-METHYLPYRIMIDINONES
    UEDA, T
    SHIBATA, Y
    KATO, Y
    SAKAKIBARA, J
    TETRAHEDRON, 1987, 43 (17) : 3917 - 3922
  • [38] CHEMISTRY AND BIOLOGICAL-ACTIVITY OF CERTAIN 4-SUBSTITUTED AND 3,4-DISUBSTITUTED PYRAZOLO[3,4-D]PYRIMIDINE NUCLEOSIDES
    BHAT, GA
    EARL, RA
    MONTERO, JLG
    PANZICA, RP
    TOWNSEND, LB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1976, 172 (SEP3): : 78 - 78
  • [39] NITROALKENE [4+2] CYCLOADDITION AS A GENERAL AND STEREOSELECTIVE ROUTE TO THE SYNTHESIS OF 3,3-DISUBSTITUTED AND 3,4-DISUBSTITUTED PYRROLIDINES
    DENMARK, SE
    MARCIN, LR
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15): : 3857 - 3868
  • [40] SYNTHESIS OF 3,4-DISUBSTITUTED BENZOFURANS VIA THE INTRAMOLECULAR COUPLING OF A ZIRCONOCENE BENZYNE COMPLEX WITH ALKENES AND ALKYNES
    COX, D
    BUCHWALD, SL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 202 : 217 - ORGN
12345