Palladium catalysed queuing processes. Part 1: Termolecular cyclization-anion capture employing carbon monoxide as a relay switch and hydride, organotin(IV) or boron reagents

被引:48
作者
Brown, S
Clarkson, S
Grigg, R [1 ]
Thomas, WA
Sridharan, V
Wilson, DM
机构
[1] Univ Leeds, MIDAS Ctr, Leeds LS2 9JT, W Yorkshire, England
[2] AstraZeneca, Huddersfield HD2 1FF, W Yorkshire, England
基金
英国工程与自然科学研究理事会;
关键词
cascade reactions; palladium catalysis; cyclization; carboformylation; Stille coupling;
D O I
10.1016/S0040-4020(00)01103-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The concept of relay switch reactants, which substantially enhance the scope of our cyclization-anion capture methodology, is introduced and exemplified by a wide variety of catalytic cyclization-carbonylation-anion capture processes employing hydride, organostannanes and NaBPh4 as anion capture agents. Mono- and bis-cyclization processes forming 5- and 6-membered rings are described, all of which employ CO at atmospheric pressure. Cyclocarboformylation processes provide interesting analogues of hydroformylation. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1347 / 1359
页数:13
相关论文
共 23 条
  • [1] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions
    Amatore, C
    Jutand, A
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) : 314 - 321
  • [2] Palladium catalysed queuing processes. Part 2: Termolecular cyclization-anion capture employing carbon monoxide as a relay switch with in situ generated vinylstannanes
    Anwar, U
    Casaschi, A
    Grigg, R
    Sansano, JM
    [J]. TETRAHEDRON, 2001, 57 (07) : 1361 - 1367
  • [3] PALLADIUM-CATALYZED CYCLIZATION CARBOFORMYLATION - MOLECULAR QUEUING CASCADES
    BROWN, S
    CLARKSON, S
    GRIGG, R
    SRIDHARAN, V
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (11) : 1135 - 1136
  • [4] PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES
    BURNS, B
    GRIGG, R
    SANTHAKUMAR, V
    SRIDHARAN, V
    STEVENSON, P
    WORAKUN, T
    [J]. TETRAHEDRON, 1992, 48 (35) : 7297 - 7320
  • [5] SEQUENTIAL AND CASCADE [2+2]-CYCLOADDITION-PALLADIUM CATALYZED CYCLIZATION - BICYCLIC BETA-LACTAMS
    BURWOOD, M
    DAVIES, B
    DIAZ, I
    GRIGG, R
    MOLINA, P
    SRIDHARAN, V
    HUGHES, M
    [J]. TETRAHEDRON LETTERS, 1995, 36 (49) : 9053 - 9056
  • [6] Palladium catalysed tandem cyclisation-anion capture. Part 5: Cascade hydrostannylation-bis-cyclisation-intramolecular anion capture. Synthesis of bridged- and spiro-cyclic small and macrocyclic heterocycles
    Casaschi, A
    Grigg, R
    Sansano, JM
    Wilson, D
    Redpath, J
    [J]. TETRAHEDRON, 2000, 56 (38) : 7541 - 7551
  • [7] Palladium catalysed tandem cyclisation-anion capture.: Part 6:: Synthesis of sugar, nucleoside, purine, benzodiazepinone and β-lactam analogues via capture of in situ generated vinylstannanes
    Casaschi, A
    Grigg, R
    Sansano, JM
    [J]. TETRAHEDRON, 2000, 56 (38) : 7553 - 7560
  • [8] El Ali B, 2000, SYNLETT, P161
  • [9] Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01
  • [10] Palladium catalysed tandem cyclisation-anion capture processes. Part 4: Organotin(IV) transfer agents
    Fretwell, P
    Grigg, R
    Sansano, JM
    Sridharan, V
    Sukirthalingam, S
    Wilson, D
    Redpath, J
    [J]. TETRAHEDRON, 2000, 56 (38) : 7525 - 7539