One-Pot, Tandem Wittig Hydrogenation: Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope

被引：7
|
作者：
Devlin, Rory [1 ,2 ]
Jones, David J. [1 ,2 ]
McGlacken, Gerard P. [1 ,2 ,3 ]
机构：
[1] Univ Coll Cork, Sch Chem, Cork T12 YN60, Ireland
[2] Univ Coll Cork, Analyt & Biol Chem Res Facil ABCRF, Cork T12 YN60, Ireland
[3] Univ Coll Cork, Synth & Solid State Pharmaceut Ctr SSPC, Cork T12 YN60, Ireland
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 13期
基金：
爱尔兰科学基金会;
关键词：
EMPLOYING STABILIZED YLIDES; LAPATINIB DERIVATIVES; ALDEHYDES; DESIGN; WATER;
D O I：
10.1021/acs.orglett.0c01874
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp(3))-C(sp(3)) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (+/-)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.
引用
收藏
页码：5223 / 5228
页数：6
相关论文
共 50 条
  • [1] Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation
    Chen, Zhen
    Rong, Meng-Yu
    Nie, Jing
    Zhu, Xue-Feng
    Shi, Bing-Feng
    Ma, Jun-An
    CHEMICAL SOCIETY REVIEWS, 2019, 48 (18) : 4921 - 4942
  • [2] Advances on Nickel-Catalyzed C(sp3)-C(sp3) Bond Formation
    Cheng Lei
    Zhou Qilin
    ACTA CHIMICA SINICA, 2020, 78 (10) : 1017 - 1029
  • [3] A decarbonylative approach to alkylnickel intermediates and C(sp3)-C(sp3) bond formation
    Huang, Zhidao
    Akana, Michelle E.
    Sanders, Kyana M.
    Weix, Daniel J.
    SCIENCE, 2024, 385 (6715) : 1331 - 1337
  • [4] Rhodium(I)-Catalyzed Sequential C(sp)C(sp3) and C(sp3)C(sp3) Bond Formation through Migratory Carbene Insertion
    Xia, Ying
    Feng, Sheng
    Liu, Zhen
    Zhang, Yan
    Wang, Jianbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (27) : 7891 - 7894
  • [5] Asymmetric allylic C(sp3)-C(sp3) bond functionalization
    He, Zhi-Tao
    NATURE SYNTHESIS, 2024, 3 (08): : 941 - 942
  • [6] Development of an Automated Platform for C(sp3)-C(sp3) Bond Formation via XAT Chemistry
    Pijper, Brenda
    Abdiaj, Irini
    Leonori, Daniele
    Alcazar, Jesus
    CHEMCATCHEM, 2023, 15 (04)
  • [7] Recent Advances in C(sp3)-C(sp3) and C(sp3)-C(sp2) Bond Formation through Cathodic Reactions: Reductive and Convergent Paired Electrolyses
    Claraz, Aurelie
    Masson, Geraldine
    ACS ORGANIC & INORGANIC AU, 2022, 2 (02): : 126 - 147
  • [8] Photoinduced Nickel-Catalyzed Deaminative Cross-Electrophile Coupling for C(sp2)-C(sp3) and C(sp3)-C(sp3) Bond Formation
    Yang, Tao
    Wei, Yi
    Koh, Ming Joo
    ACS CATALYSIS, 2021, 11 (11): : 6519 - 6525
  • [9] Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)-C(sp3)/C(sp3)-C(sp2) Bond Formation and Mechanistic Studies
    Shekhar, K. C.
    Dhungana, Roshan K.
    Shrestha, Bijay
    Thapa, Surendra
    Khanal, Namrata
    Basnet, Prakash
    Lebrun, Robert W.
    Giri, Ramesh
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (31) : 9801 - 9805
  • [10] The Formation of C( sp3 )-C( sp3 ) by Visible-Light Photocatalysis
    Yi, Xiangyan
    Huang, Fei
    Baell, Jonathan B.
    Huang, He
    Yu, Yang
    PROGRESS IN CHEMISTRY, 2019, 31 (04) : 505 - 515
12345