Benchtop monitoring of reaction progress via visual recognition with a handheld UV lamp: In situ monitoring of boronic acids in the Suzuki-Miyaura reaction

被引:23
作者
Barder, Timothy E. [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ol062802q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Although boronic acids are widely used in metal-catalyzed reactions, it is difficult to assay their consumption. As such, we developed a reversible fluorescent sensor that is activated upon binding a boronic acid. The sensor can be used to monitor consumption of a boronic acid in Suzuki-Miyaura reactions. Importantly, only a standard handheld long-wave UV lamp (365 nm) is required and fluorescence is easily detectable with the naked eye without disturbing the reaction mixture.
引用
收藏
页码:137 / 139
页数:3
相关论文
共 14 条
  • [1] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
    Barder, TE
    Walker, SD
    Martinelli, JR
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4685 - 4696
  • [2] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances
    Bellina, F
    Carpita, A
    Rossi, R
    [J]. SYNTHESIS-STUTTGART, 2004, (15): : 2419 - 2440
  • [3] SPECTROFLUOROMETRIC DETERMINATION OF BORON IN SOILS, PLANTS AND NATURAL-WATERS WITH ALIZARIN RED-S
    CAMPANA, AMG
    BARRERO, FA
    CEBA, MR
    [J]. ANALYST, 1992, 117 (07) : 1189 - 1191
  • [4] Chan DMT, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P205, DOI 10.1002/3527606548.ch5
  • [5] FLOW-INJECTION SPECTROFLUOROMETRIC DETERMINATION OF BORON USING ALIZARIN-RED-S IN AQUEOUS-SOLUTION
    CHIMPALEE, N
    CHIMPALEE, D
    BOONYANITCHAYAKUL, B
    BURNS, DT
    [J]. ANALYTICA CHIMICA ACTA, 1993, 282 (03) : 643 - 646
  • [6] Grasselli J.G., 1973, CRC ATLAS SPECTRAL D
  • [7] Hall DG, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P1, DOI 10.1002/3527606548
  • [8] Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions
    Hayashi, T
    Yamasaki, K
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2829 - 2844
  • [9] Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis
    Kotha, S
    Lahiri, K
    Kashinath, D
    [J]. TETRAHEDRON, 2002, 58 (48) : 9633 - 9695
  • [10] RUDAKOVA IS, 1963, UCH ZAP I FARMAKOL K, V3, P316