Palladium-catalyzed bicyclization of alkynyl aryl iodide with allenyl malonates

被引:4
|
作者
Zhou, Ping-Xin [1 ]
Liu, Yang [1 ]
Du, Xueyan [1 ]
Liu, Ning [1 ]
Li, Kexin [2 ]
Wu, Yuji [1 ]
Feng, Wang [1 ]
Liu, Xu [2 ]
Kong, Yingying [1 ]
机构
[1] Xinxiang Med Univ, Sch Basic Med Sci, Xinxiang 453003, Henan, Peoples R China
[2] Xinxiang Med Univ, Sch Pharm, Xinxiang 453003, Henan, Peoples R China
关键词
COUPLING-CYCLIZATION REACTION; TOSYLHYDRAZONE INSERTION REACTION; STEREOSELECTIVE-SYNTHESIS; N-TOSYLHYDRAZONES; NUCLEOPHILIC FUNCTIONALITY; SELECTIVE FORMATION; CASCADE REACTIONS; ACCESS; BONDS; REGIOSELECTIVITY;
D O I
10.1039/d3qo01169k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed highly regio- and stereoselective reaction of alkynyl aryl iodide with allenyl malonates was realized to afford a series of bicyclic compounds. The cascade process involves intramolecular carbopalladation of internal alkynes/intermolecular carbopalladation of allenes/cyclization. This new approach has good functional group compatibility and broad substrate scope.
引用
收藏
页码:5451 / 5456
页数:6
相关论文
共 50 条
  • [1] Palladium-Catalyzed Bicyclization of 1-(2,2-Dibromovinyl)-2-Alkenylbenzene with Allenyl Malonates
    Zhou, Ping-Xin
    Liu, Yang
    Wang, Cui-Tian
    Li, Kexin
    Ren, Feng
    Tan, Xinqiang
    Liang, Yong-Min
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (19) : 4109 - 4113
  • [2] Palladium-Catalyzed Decarboxylative Trifluoroethylation of Aryl Alkynyl Carboxylic Acids
    Hwang, Jinil
    Park, Kyungho
    Choe, Juseok
    Min, Hongkeun
    Song, Kwang Ho
    Lee, Sunwoo
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (07): : 3267 - 3271
  • [3] Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Tosylates
    Lee, Ju-Hyeon
    Raja, Gabriel Charles Edwin
    Yu, Subeen
    Lee, Junseong
    Song, Kwang Ho
    Lee, Sunwoo
    ACS OMEGA, 2017, 2 (09): : 6259 - 6269
  • [4] Theoretical studies of palladium-catalyzed cycloaddition of alkynyl aryl ethers and alkynes
    Qingxi Meng
    Fen Wang
    Journal of Molecular Modeling, 2014, 20
  • [5] Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Aryl Halides
    Moon, Jeongju
    Jang, Mihee
    Lee, Sunwoo
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03): : 1403 - 1406
  • [6] Theoretical studies of palladium-catalyzed cycloaddition of alkynyl aryl ethers and alkynes
    Meng, Qingxi
    Wang, Fen
    JOURNAL OF MOLECULAR MODELING, 2014, 20 (12)
  • [7] Stereochemistry of palladium-catalyzed asymmetric transformation of chiral 2-alkynyl sulfinates into allenyl sulfones
    Hiroi, K
    Kato, F
    Nakasato, H
    CHEMISTRY LETTERS, 1998, (06) : 553 - 554
  • [8] PALLADIUM-CATALYZED REARRANGEMENT OF 2-ALKYNYL ARYL KETONES TO SUBSTITUTED FURANS
    SHENG, H
    LIN, S
    HUANG, Y
    SYNTHESIS-STUTTGART, 1987, (11): : 1022 - 1023
  • [9] Stereochemical studies of the palladium-catalyzed rearrangements of chiral 2-alkynyl sulfinates into chiral allenyl sulfones
    Hiroi, K
    Kato, F
    TETRAHEDRON, 2001, 57 (08) : 1543 - 1550
  • [10] Access to β-Keto Esters by Palladium-Catalyzed Carbonylative Coupling of Aryl Halides with Monoester Potassium Malonates
    Korsager, Signe
    Nielsen, Dennis U.
    Taaning, Rolf H.
    Skrydstrup, Troels
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) : 9763 - 9766