Indium-mediated allylation of carbonyl compounds in deep eutectic solvents

被引:7
|
作者
Gonzalez-Gallardo, Nerea
Saavedra, Beatriz
Guillena, Gabriela [1 ,2 ]
Ramon, Diego J. [1 ,2 ]
机构
[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Apdo 99, Alicante 03080, Spain
[2] Univ Alicante, Fac Ciencias, Inst Sintesis Organ ISO, Apdo 99, Alicante 03080, Spain
关键词
allylation; green chemistry; indium; solvent effects; sustainability; RECOMBINATION EFFICIENCIES; BARBIER ALLYLATION; ORGANIC-SYNTHESIS; IONIC LIQUIDS; ALDEHYDES; KETONES; TOXICITY; MICROVISCOSITY; ORGANOLITHIUM; CHEMISTRY;
D O I
10.1002/aoc.6418
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
This study describes, for the first time, the in situ generation of indium organometallic reagents in environmentally friendly deep eutectic solvents (DESs). The allylation process of different carbonyl compounds is achieved mediated by indium metal and using cheap allyl chloride derivatives. The unique DES properties allow to perform the reaction at room temperature and under air, obtaining yields ranging from 45% to 99%. It is possible to recycle the reaction medium for at least four consecutive cycles without much decrease of the observed results. Also, a linear correlation between the yield of the reaction and the density of the DESs is observed.
引用
收藏
页数:9
相关论文
共 50 条
  • [21] Enantioselective palladium/indium-mediated allylation of aldehydes.
    Cook, GR
    Xu, W
    Sun, LD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U575 - U575
  • [22] Studies towards total synthesis of antillatoxin: Indium-mediated allylation reaction of carbonyl compounds with secondary allylic bromide in aqueous media
    Loh, TP
    Song, HY
    SYNLETT, 2002, (12) : 2119 - 2121
  • [23] Highly diastereoselective indium-mediated allylation of chiral hydrazones
    Cook, GR
    Maity, BC
    Kargbo, R
    ORGANIC LETTERS, 2004, 6 (11) : 1741 - 1743
  • [24] Indium-mediated allylation reaction of difluoroacetyltrialkylsilanes in aqueous media
    Chung, WJ
    Higashiya, S
    Welch, JT
    TETRAHEDRON LETTERS, 2002, 43 (33) : 5801 - 5803
  • [25] A highly enantioselective indium-mediated allylation reaction of aldehydes
    Loh, TP
    Zhou, JR
    Yin, Z
    ORGANIC LETTERS, 1999, 1 (11) : 1855 - 1857
  • [26] Highly enantioselective catalytic indium-mediated allylation of hydrazones
    Cook, Gregory R.
    Kargbo, Robert
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [27] Indium-mediated allylation of hydroxyphthalides with acetic acid as an additive
    Lee, JH
    Park, YS
    Nam, MH
    Lee, SH
    Cho, MY
    Yoon, CM
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2005, 26 (03) : 496 - 498
  • [28] Indium-mediated allylation of 1,2-diketones
    Kang, SK
    Baik, TG
    Jiao, XH
    SYNTHETIC COMMUNICATIONS, 2002, 32 (01) : 75 - 78
  • [29] Indium-mediated allylation of α-imino esters in aqueous media
    Piao, Xiane
    Jung, Jae-Kyung
    Kang, Han-Young
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2007, 28 (01) : 139 - 142
  • [30] Indium-mediated allylation of carbonyl compounds with an allylic bromide in aqueous media:: anomalous syn-diastereoselectivity regardless of allylic bromide geometry
    Loh, TP
    Yin, Z
    Song, HY
    Tan, KL
    TETRAHEDRON LETTERS, 2003, 44 (05) : 911 - 914