TsNBr2 mediated oxidative functionalization of alkynes

被引：28
作者：
Rajbongshi, Kamal Krishna [1 ]
Hazarika, Debojit [1 ]
Phukan, Prodeep [1 ]
机构：
[1] Gauhati Univ, Dept Chem, Gauhati 781014, Assam, India
来源：
TETRAHEDRON | 2016年 / 72卷 / 29期
关键词：
TsNBr2; Alkyne; Ketone; alpha-Bromoketone; 1-Bromoalkyne; HYPERVALENT IODINE REAGENT; ONE-STEP SYNTHESIS; ONE-POT SYNTHESIS; TERMINAL ALKYNES; STEREOSELECTIVE-SYNTHESIS; CATALYZED HYDRATION; EFFICIENT SYNTHESIS; ALPHA-BROMOKETONES; REGIOSELECTIVE HYDRATION; SELECTIVE DEBROMINATION;
D O I：
10.1016/j.tet.2016.05.017
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new approach has been developed for oxidative transformation of alkynes by controlled manipulation of TsNBr2 mediated process. Alkynes could be readily converted to ketones and alpha-bromoketones via an oxybromination debromination sequence. When alkynes are treated successively with TsNBr2, KI and Na2SO3 in a mixture of acetone and water at room temperature, corresponding ketones were obtained. On the other hand, treatment of alkynes with TsNBr2 and Na2SO3 in a mixture of ethyl acetate, acetone and water at room temperature could produce corresponding alpha-bromoketones. 1-Bromoalkynes could also be synthesized from corresponding alkynes within a very short time using TsNBr2 at room temperature. In all cases, excellent yields of corresponding products are obtained. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4151 / 4158
页数：8
相关论文
共 98 条
  • [1] Mild and selective phase transfer catalysed bromination of terminal acetylenes using carbon tetrabromide as reagent
    Abele, E
    Rubina, K
    Abele, R
    Gaukhman, A
    Lukevics, E
    [J]. JOURNAL OF CHEMICAL RESEARCH, 1998, (09) : 618 - 619
  • [2] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
    Alonso, F
    Beletskaya, IP
    Yus, M
    [J]. CHEMICAL REVIEWS, 2004, 104 (06) : 3079 - 3159
  • [3] Synthesis and reactivity of indenyl ruthenium(II) complexes containing the labile ligand 1,5-cyclooctadiene (COD):: Catalytic activity of [Ru(η5-C9H7)Cl(COD)]
    Alvarez, P
    Gimeno, J
    Lastra, E
    García-Granda, S
    Van der Maelen, JF
    Bassetti, M
    [J]. ORGANOMETALLICS, 2001, 20 (17) : 3762 - 3771
  • [4] Application of copper(I)-catalysed azide/alkyne cycloaddition (CuAAC) 'click chemistry' in carbohydrate drug and neoglycopolymer synthesis
    Aragao-Leoneti, Valquiria
    Campo, Vanessa L.
    Gomes, Adriane S.
    Field, Robert A.
    Carvalho, Ivone
    [J]. TETRAHEDRON, 2010, 66 (49) : 9475 - 9492
  • [5] Photochemical α-bromination of ketones using N-bromosuccinimide:: a simple, mild and efficient method
    Arbuj, Sudhir S.
    Waghmode, Suresh B.
    Ramaswamy, A. V.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (08) : 1411 - 1415
  • [6] Parallel synthesis of novel heteroaromatic acromelic acid analogues from kainic acid
    Baldwin, JE
    Fryer, AM
    Pritchard, GJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) : 2588 - 2596
  • [7] Prenylflavonoids and prenyl/alkyl-phloroacetophenones: Synthesis and antitumour biological evaluation
    Basabe, P.
    de Roman, M.
    Marcos, I. S.
    Diez, D.
    Blanco, A.
    Bodero, O.
    Mollinedo, F.
    Sierra, B. G.
    Urones, J. G.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) : 4258 - 4269
  • [8] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends
    Beller, M
    Seayad, J
    Tillack, A
    Jiao, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) : 3368 - 3398
  • [9] Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes
    Boden, CDJ
    Pattenden, G
    Ye, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (20): : 2417 - 2419
  • [10] Efficient synthesis of methyl carbamate via Hofmann rearrangement in the presence of TsNBr2
    Borah, Arun Jyoti
    Phukan, Prodeep
    [J]. TETRAHEDRON LETTERS, 2012, 53 (24) : 3035 - 3037
12345678910