Bite angle effect of bidentate P-N ligands in palladium catalysed allylic alkylation

被引：44
|
作者：
van Haaren, RJ
Druijven, CJM
van Strijdonck, GPF
Oevering, H
Reek, JNH
Kamer, PCJ
van Leeuwen, PWNM
机构：
[1] Univ Amsterdam, Fac Chem, Inst Mol Chem, NL-1018 WV Amsterdam, Netherlands
[2] DSM Res BV, NL-6160 MD Geleen, Netherlands
来源：
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS | 2000年 / 10期
关键词：
D O I：
10.1039/b001355m
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Two series of new bidentate P-N ligands have been synthesized. Application of these ligands in the palladium catalysed allylic alkylation of crotyl chloride and cinnamyl chloride leads to the preferential formation of the branched product. A larger bite angle of the ligand leads to higher regioselectivity. Stoichiometric alkylation of the complex [Pd(C4H7){p-MeOC6H4C=N(CH2)(4)OPPh2}][O3SCF3] proceeds with 88% regioselectivity to the branched product.
引用
收藏
页码：1549 / 1554
页数：6
相关论文
共 50 条
  • [21] Regiocontrol in palladium-catalysed allylic alkylation by addition of lithium iodide
    Kawatsura, M
    Uozumi, Y
    Hayashi, T
    CHEMICAL COMMUNICATIONS, 1998, (02) : 217 - 218
  • [22] Heterodimetallic palladium(II) complexes with bidentate (N,S) or terdentate (C,N,S)- ferrocenyl ligands.: The effect of the ligand donor atoms on the regioselectivity of the allylic alkylation of cinnamyl acetate
    Lopez, Concepcion
    Perez, Sonia
    Solans, Xavier
    Font-Bardia, Merce
    Roig, Anna
    Molins, Elies
    van Leeuwen, Piet W. N. M.
    van Strijdonck, Gino P. F.
    ORGANOMETALLICS, 2007, 26 (03) : 571 - 576
  • [23] Palladium-catalysed annulative allylic alkylation for the synthesis of benzannulated heteroarenes
    Yadav, Sonu
    Ramasastry, S. S. V.
    CHEMICAL COMMUNICATIONS, 2021, 57 (01) : 77 - 80
  • [24] Chiral oxazolinylpyridines as ligands for enantioselective palladium catalysed allylic substitution
    Chelucci, G
    Medici, S
    Saba, A
    TETRAHEDRON-ASYMMETRY, 1997, 8 (19) : 3183 - 3184
  • [25] New P,N-ferrocenyl ligands for rhodium-catalyzed hydroboration and palladium-catalyzed allylic alkylation
    Kloetzing, RJ
    Lotz, M
    Knochel, P
    TETRAHEDRON-ASYMMETRY, 2003, 14 (02) : 255 - 264
  • [26] OPENING OF THE P-N BOND OF BICYCLIC PHOSPHORANES .8. THE DRAMATIC EFFECT OF BIDENTATE P(III)-N(III) LIGANDS ON THE COURSE OF PALLADIUM-CATALYZED OLIGOMERIZATION OF BUTADIENE
    AGBOSSOU, S
    BONNET, MC
    TKATCHENKO, I
    NOUVEAU JOURNAL DE CHIMIE-NEW JOURNAL OF CHEMISTRY, 1985, 9 (05): : 311 - 314
  • [27] Biimidazoline ligands for palladium-catalyzed asymmetric allylic alkylation
    Hao, Xin-Qi
    Dong, Ya-Nan
    Gao, Biao
    Li, Ke
    Zhao, Xue-Mei
    Xu, Yan
    Song, Mao-Ping
    TETRAHEDRON-ASYMMETRY, 2015, 26 (23) : 1360 - 1368
  • [28] Versatile ligands for palladium-catalyzed asymmetric allylic alkylation
    Dierkes, P
    Ramdeehul, S
    Barloy, L
    De Cian, A
    Fischer, J
    Kamer, PCJ
    van Leeuwen, PWNM
    Osborn, JA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (22) : 3116 - 3118
  • [29] Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams
    Behenna, Douglas C.
    Liu, Yiyang
    Yurino, Taiga
    Kim, Jimin
    White, David E.
    Virgil, Scott C.
    Stoltz, Brian M.
    NATURE CHEMISTRY, 2012, 4 (02) : 130 - 133
  • [30] Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams
    Douglas C. Behenna
    Yiyang Liu
    Taiga Yurino
    Jimin Kim
    David E. White
    Scott C. Virgil
    Brian M. Stoltz
    Nature Chemistry, 2012, 4 (2) : 130 - 133
12345