Palladium-Catalyzed Unimolecular Fragment Coupling of N -Allylamides Bearing a Tethered Nucleophile with the Translocation of an Amide Group

被引:5
|
作者
Shimazumi, Ryoma [1 ]
Kodama, Takuya [1 ,2 ]
Tobisu, Mamoru [1 ,2 ]
机构
[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Inst Open & Transdisciplinary Res Initiat ICS OTRI, Innovat Catalysis Sci Div, Suita, Osaka 5650871, Japan
来源
SYNTHESIS-STUTTGART | 2023年 / 56卷 / 01期
基金
日本科学技术振兴机构; 日本学术振兴会;
关键词
palladium catalyst; C-N bond activation; amides; isocyanates; elimination; rearrangement; ALKENES; BONDS;
D O I
10.1055/a-2022-1905
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed reaction of N-allylamides bearing a tethered nucleophile results in the extrusion of an amide moiety in the form of an isocyanate, with its subsequent capture by the pendant nucleophile. This reaction involves the net catalytic transposition of an amide group.
引用
收藏
页码:134 / 142
页数:9
相关论文
共 50 条
  • [31] Amide as an efficient ligand in the palladium-catalyzed Suzuki coupling reaction in water/ethanol under aerobic conditions
    Liu, Hai Yang
    Wang, Kun
    Fu, Hai Yan
    Yuan, Mao Lin
    Chen, Hua
    Li, Rui Xiang
    CHINESE CHEMICAL LETTERS, 2011, 22 (06) : 738 - 740
  • [32] SCOPE OF THE PALLADIUM-CATALYZED COUPLING REACTION OF ORGANOMETALLICS WITH ALLYLIC ELECTROPHILES - EFFECT OF THE LEAVING GROUP
    NEGISHI, E
    CHATTERJEE, S
    MATSUSHITA, H
    TETRAHEDRON LETTERS, 1981, 22 (38) : 3737 - 3740
  • [33] Simultaneous Reduction of Aldehyde Group to Hydroxymethyl Group in Palladium-catalyzed Suzuki Cross-coupling Reaction
    Wang Yingchun
    Li Xiuying
    Li Yajun
    Pan Yingming
    Cheng Keguang
    Wang Hengshan
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2014, 30 (04) : 614 - 618
  • [34] Simultaneous reduction of aldehyde group to hydroxymethyl group in palladium-catalyzed Suzuki cross-coupling reaction
    Yingchun Wang
    Xiuying Li
    Yajun Li
    Yingming Pan
    Keguang Cheng
    Hengshan Wang
    Chemical Research in Chinese Universities, 2014, 30 : 614 - 618
  • [35] Hetaryl Bromides Bearing the SO2F Group - Versatile Substrates for Palladium-Catalyzed C-C Coupling Reactions
    Cherepakha, Artem Yu.
    Stepannikova, Kateryna O.
    Vashchenko, Bohdan V.
    Gorichko, Marian V.
    Tolmachev, Andrey A.
    Grygorenko, Oleksandr O.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (47) : 6682 - 6692
  • [36] Palladium-catalyzed nucleophile-alkyne-alpha,beta-unsaturated carbonyl coupling through tandem nucleopalladation and conjugate addition
    Wang, Z
    Lu, XY
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07): : 2254 - 2255
  • [37] Synthesis of fluoroaniline derivatives by selective palladium-catalyzed coupling of N-methylpiperazine and fluorohaloarenes
    Hayden, S
    Sowa, JR
    CATALYSIS OF ORGANIC REACTIONS, 1998, 75 : 627 - 632
  • [38] Palladium-catalyzed coupling reactions involving N-alkoxyimidoyl halides and boronic acids
    Dolliver, Debra D.
    Poche, Caroline
    Johnson, James E.
    Mckim, Artie S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [39] Palladium-Catalyzed Heck-Type Coupling via C-N Cleavage
    Fan, Weizheng
    Liu, Faming
    Feng, Bainian
    SYNLETT, 2015, 26 (09) : 1253 - 1257
  • [40] Synthesis of 1,4-Benzodiazepines by Palladium-Catalyzed C-N Coupling
    Bhardwaj, Pranshu
    Kaur, Navjeet
    CURRENT ORGANIC CHEMISTRY, 2023, 27 (04) : 282 - 296