Palladium-Catalyzed Oxidative Cross-Coupling of Conjugated Enynones with Allylarenes: Synthesis of Furyl-Substituted 1,3-Dienes

被引:16
|
作者
Ping, Yifan [1 ]
Zhang, Sudong [1 ]
Chang, Taiwei [1 ]
Wang, Jianbo [1 ,2 ]
机构
[1] Peking Univ, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China
[2] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 12期
关键词
ENE-YNE-KETONES; C-H AMINATION; SERIAL LIGAND CATALYSIS; METAL CARBENE; TERMINAL ALKENES; DIAZO-COMPOUNDS; ALLYL HALIDES; OLEFINS; TOSYLHYDRAZONES; ALKYLATION;
D O I
10.1021/acs.joc.9b00922
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of furyl-substituted 1,3-dienes via palladium-catalyzed oxidative cross coupling of conjugated enynones with allylarenes is developed. This reaction shows broad substrate scope and good functional group tolerance. Palladium carbene migratory insertion is proposed as the key step for this transformation with conjugated enynones serving as the carbene precursors.
引用
下载
收藏
页码:8275 / 8283
页数:9
相关论文
共 50 条
  • [21] Palladium-catalyzed synthesis of 1,3-dienes from allenes and organic halides
    Chang, HM
    Cheng, CH
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06): : 1767 - 1773
  • [22] A NOVEL PALLADIUM-CATALYZED DEOXYGENATION OF ENEDIOLS TO 1,3-DIENES
    TROST, BM
    TOMETZKI, GB
    SYNTHESIS-STUTTGART, 1991, (12): : 1235 - 1245
  • [23] PALLADIUM-CATALYZED DECARBONYLATIVE COUPLING OF ACID-CHLORIDES, ORGANODISILANES, AND 1,3-DIENES
    OBORA, Y
    TSUJI, Y
    KAWAMURA, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) : 10414 - 10415
  • [24] PALLADIUM-CATALYZED CARBOANNULATION OF 1,3-DIENES BY ARYL HALIDES
    LAROCK, RC
    FRIED, CA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (15) : 5882 - 5884
  • [25] Palladium-Catalyzed Asymmetric Dihydroxylation of 1,3-Dienes with Catechols
    Fan, Tao
    Shen, Hong-Cheng
    Han, Zhi-Yong
    Gong, Liu-Zhu
    CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (03) : 226 - 232
  • [26] Palladium-catalyzed hydrophosphorylation of 1,3-dienes leading to allylphosphonates
    Mirzaei, F
    Han, LB
    Tanaka, M
    TETRAHEDRON LETTERS, 2001, 42 (02) : 297 - 299
  • [27] Nickel-catalyzed cross-coupling of dienyl phosphates with Grignard reagents in the synthesis of 2-substituted 1,3-dienes
    Sofia, A
    Karlström, E
    Itami, K
    Bäckvall, JE
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05): : 1745 - 1749
  • [28] Nickel-catalyzed cross-coupling of dienyl phosphates with Grignard reagents in the synthesis of 2-substituted 1,3-dienes
    Karlstrom, A. Sofia E.
    Itami, Kenichiro
    Backvall, Jan-E
    Journal of Organic Chemistry, 1999, 64 (2-5): : 1745 - 1749
  • [29] Highly efficient synthesis of 1,1-difluoro-2-substituted-1,3-dienes and dienynes from gem-difluorohomoallenyl bromide via palladium-catalyzed cross-coupling reactions
    Shen, QL
    Hammond, GB
    ORGANIC LETTERS, 2001, 3 (14) : 2213 - 2215
  • [30] Iron-Catalyzed Cross-Coupling of α-Allenyl Esters with Grignard Reagents for the Synthesis of 1,3-Dienes
    Kong, Wei-Jun
    Kessler, Simon N.
    Wu, Haibo
    Backvall, Jan-E
    ORGANIC LETTERS, 2023, : 120 - 124