Direct coupling of sp3 carbon of alkanes with α,β-unsaturated carbonyl compounds using a copper/hydroperoxide system

被引：29
|
作者：
Lan, Yun [1 ]
Yang, Chao [1 ]
Xu, Yun-He [1 ]
Loh, Teck-Peng [1 ,2 ]
机构：
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637616, Singapore
来源：
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 07期
基金：
中国国家自然科学基金;
关键词：
C-H BONDS; CYCLIC ETHERS; C(SP(3))-H ACTIVATION; HETEROCYCLE SYNTHESIS; OXIDATIVE ACTIVATION; UNACTIVATED ALKANES; ORGANIC-MOLECULES; RADICAL REACTIONS; C(SP(2))-H BONDS; FUNCTIONALIZATION;
D O I：
10.1039/c7qo00149e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new methodology for the monovalent copper-initiated direct coupling of alkanes and hydroperoxides with unsaturated carbonyl compounds is developed. In this work, alpha, beta-unsaturated carbonyl compounds underwent alkylation and peroxidation to give synthetically useful a-peroxy ketones with wide functional group tolerance. The resulting alpha-peroxy ketones could be easily transformed into very useful a-hydroxy ketones.
引用
收藏
页码：1411 / 1415
页数：5
相关论文
共 50 条
  • [31] Convenient C(sp3)-H bond functionalisation of light alkanes and other compounds by iron photocatalysis
    Jin, Yunhe
    Zhang, Qingqing
    Wang, Lifang
    Wang, Xinyao
    Meng, Changgong
    Duan, Chunying
    GREEN CHEMISTRY, 2021, 23 (18) : 6984 - 6989
  • [32] Direct β-C(sp3)-H Functionalization of Aliphatic Amines to α,β-Unsaturated Imines, Aldehydes, and Chromenes
    Mandal, Sumana
    Mahato, Sujit
    Jana, Chandan K.
    ORGANIC LETTERS, 2015, 17 (15) : 3762 - 3765
  • [33] Copper-catalyzed direct α-ketoesterification of propiophenones with acetophenones via C(sp3)-H oxidative cross-coupling
    Du, Juan
    Zhang, Xiuli
    Sun, Xi
    Wang, Lei
    CHEMICAL COMMUNICATIONS, 2015, 51 (21) : 4372 - 4375
  • [34] Decarboxylative sp3 C–N coupling via dual copper and photoredox catalysis
    Yufan Liang
    Xiaheng Zhang
    David W. C. MacMillan
    Nature, 2018, 559 : 83 - 88
  • [35] Nickel-Catalyzed Cross-Dehydrogenative Coupling of α-C(sp3)-H Bonds in N-Methylamides with C(sp3)-H Bonds in Cyclic Alkanes
    Li, Ze-Lin
    Sun, Kang-Kang
    Cai, Chun
    ORGANIC LETTERS, 2018, 20 (20) : 6420 - 6424
  • [36] Copper-catalyzed oxidative C(sp3)-H/N-H coupling of sulfoximines and amides with simple alkanes via a radical process
    Teng, Fan
    Sun, Song
    Jiang, Yan
    Yu, Jin-Tao
    Cheng, Jiang
    CHEMICAL COMMUNICATIONS, 2015, 51 (27) : 5902 - 5905
  • [37] Ni-catalyzed C(sp3)-C(sp3) cross-coupling to access γ-carbonyl alkylboronates and alkylsilicons enabled by cyclopropanol-derived homoenolates
    Zhu, Linfei
    Sun, Yang
    Wang, Hui
    ORGANIC CHEMISTRY FRONTIERS, 2025,
  • [38] Deoxygenative Insertion of Carbonyl Carbon into a C(sp3)-H Bond: Synthesis of Indolines and Indoles
    Asako, Sobi
    Ishihara, Seina
    Hirata, Keiya
    Takai, Kazuhiko
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (25) : 9832 - 9836
  • [39] meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp3)-N(sp3) Bond Formation
    Dutta, Kartik
    Wadawale, Amey P.
    Mula, Soumyaditya
    ORGANIC LETTERS, 2024, 26 (35) : 7267 - 7272
  • [40] Oxidative coupling of sp2 and sp3 carbon-hydrogen bonds to construct dihydrobenzofurans
    Shi, Jiang-Ling
    Wang, Ding
    Zhang, Xi-Sha
    Li, Xiao-Lei
    Chen, Yu-Qin
    Li, Yu-Xue
    Shi, Zhang-Jie
    NATURE COMMUNICATIONS, 2017, 8
12345