Rapid fluorous Stille coupling reactions conducted under microwave irradiation

被引:105
|
作者
Larhed, M
Hoshino, M
Hadida, S
Curran, DP
Hallberg, A
机构
[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260
[2] UNIV UPPSALA,CTR BIOMED,DEPT ORGAN PHARMACEUT CHEM,S-75123 UPPSALA,SWEDEN
来源
JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 16期
关键词
D O I
10.1021/jo970362y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed fluorous Stille cross-coupling reactions with organic halides or triflates require only 90-120 s for completion when conducted under microwave irradiation. Comparable thermal reactions require about 1 day. Fourteen different coupling products were synthesized and isolated in good yields after three-phase extraction (FC-84, dichloromethane, water) and chromatography. The examples extend the scope of the fluorous Stille coupling with respect to both the tin and halide/triflate components. Applications in parallel synthesis are suggested.
引用
收藏
页码:5583 / 5587
页数:5
相关论文
共 50 条
  • [41] Microwave-assisted Stille and Hiyama cross-coupling reactions catalyzed by ortho-palladated complexes of homoveratrylamine
    Hajipour, Abdol Reza
    Rafiee, Fatemeh
    TETRAHEDRON LETTERS, 2012, 53 (35) : 4661 - 4664
  • [42] Solid phase peptide coupling and its kinetics under microwave irradiation
    Yang, Ming
    Wang, Wei-Guo
    Li, Pei-Hua
    Zhang, Jun
    Shen, Shu-Bao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (05) : 851 - 856
  • [43] Multifield coupling study on random aggregate concrete under microwave irradiation
    Zhang, Pengju
    Wei, Wei
    Shao, Zhushan
    CONSTRUCTION AND BUILDING MATERIALS, 2022, 318
  • [44] A rapid and efficient synthesis of symmetrical disulfides under microwave irradiation conditions
    Wang, JX
    Gao, LJ
    Huang, DF
    SYNTHETIC COMMUNICATIONS, 2002, 32 (07) : 963 - 969
  • [45] Rapid and efficient synthesis of imidazolines and bisimidazolines under microwave and ultrasonic irradiation
    Moghadam, Majid
    Mohammadpoor-Baltork, Iraj
    Mirkhani, Valiollah
    Tangestaninejad, Shahram
    Abdollahi-Alibeik, Mohammad
    Yousefi, Behrooz H.
    Kargar, Hadi
    MONATSHEFTE FUR CHEMIE, 2007, 138 (06): : 579 - 583
  • [46] Rapid and Convenient Synthesis of N-Arylmorpholines under Microwave Irradiation
    Li, Hong Bo
    Liang, Wu
    Ma, Chang Peng
    Kai, Yong Mao
    Li, Lei
    Zhang, Yong Gang
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (04) : 995 - 998
  • [47] Rapid N-alkylation of benzoxazinones and benzothlazinones under microwave irradiation
    Huang, ZZ
    Zu, LS
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (01) : 121 - 123
  • [48] Rapid N-alkylation of benzoxazinones and benzothiazinones under microwave irradiation
    Department of Chemistry, University of Hangzhou, Hangzhou, 310028, China
    Org. Prep. Proc. Int., 1 (121-123):
  • [49] Rapid Decomposition of a Cationic Azo-Initiator Under Microwave Irradiation
    Costa, C.
    Santos, V. H. S.
    Araujo, P. H. H.
    Sayer, C.
    Santos, A. F.
    Dariva, C.
    Fortuny, M.
    JOURNAL OF APPLIED POLYMER SCIENCE, 2010, 118 (03) : 1421 - 1429
  • [50] A rapid and efficient synthesis of indoloquinolinone and its analogues under microwave irradiation
    Yu Jing Lu Ning Sun Zhi Shu Huang* Lian Quan Gu* School of Pharmaceutical Sciences
    Chinese Chemical Letters, 2008, (05) : 518 - 520