Regioselective C-H Activation and Sequential C-C and C-O Bond Formation Reactions of Aryl Ketones Promoted by an Yttrium Carbene

被引:98
|
作者
Mills, David P. [1 ]
Soutar, Lyndsay [1 ]
Lewis, William [1 ]
Blake, Alexander J. [1 ]
Liddle, Stephen T. [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
基金
英国工程与自然科学研究理事会;
关键词
METAL-CARBON BONDS; STRUCTURAL-CHARACTERIZATION; ALKYLIDENE COMPLEXES; CALCIUM CARBENE; REACTIVITY; METHYLIDENE; LANTHANIDES; MONOXIDE; DIANION; SYSTEM;
D O I
10.1021/ja107958u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Rare earth carbenes exclusively exhibit Wittig-type reactivity with carbonyl compounds to afford alkenes. Here, we report that yttrium carbenes can effect regioselective ortho-C-H activation and sequential C-C and C-O bond formation reactions of aryl ketones to give iso-benzofurans and hydroxymethylbenzophenones. With MeCOPh, cyclotetramerization occurs giving a substituted cyclohexene. This demonstrates new rare earth carbene reactivity which complements existing Wittig-type reactivity.
引用
收藏
页码:14379 / 14381
页数:3
相关论文
共 50 条
  • [31] Catalytic C-C Bond Formation by C-H Functionaliza C-C Bond Cleavage Preface
    Dong, Guangbin
    TETRAHEDRON, 2016, 72 (22) : 2717 - 2717
  • [32] AROMATIZATION OF C6 HYDROCARBONS BY CP-STAR-RU+ THROUGH C-H, C-C OR C-O BOND ACTIVATION
    CHAUDRET, B
    HE, XD
    LABROUE, D
    RONDON, D
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 232 - INOR
  • [33] Rhodium(III)-Catalyzed C-C Bond Formation by Direct C-H Activation
    Li, Xiaolan
    Luo, Haiqing
    SYNLETT, 2025,
  • [34] Ruthenium-catalyzed C-H activation and C-C bond formation.
    Gunnoe, TB
    Lail, M
    Arrowood, BN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U58 - U58
  • [35] Cu(II)-Mediated C-C/C-O Bond Formation via C-H/C-C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group
    Yu, Shuling
    Lv, Ningning
    Liu, Zhanxiang
    Zhang, Yuhong
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (01) : 118 - 125
  • [36] Catalytic intramolecular c-c bond formation using c-h activation.
    Thalji, RK
    Ahrendt, KA
    Bergman, RG
    Ellman, JA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U57 - U57
  • [37] CoIII-Catalyzed C-H Alkenylation and Allylation with Cyclopropenes via Sequential C-H/C-C Bond Activation
    Kim, Ye Lim
    Park, Sun-a
    Choi, Seoung-Mi
    Park, Jong-Un
    Kim, Ju Hyun
    ORGANIC LETTERS, 2021, 23 (17) : 6674 - 6679
  • [38] SELECTIVE AROMATIZATION OF THE A-RING OF STEROIDS THROUGH C-C, C-H, AND C-O BOND ACTIVATION BY AN ELECTROPHILIC RUTHENIUM COMPLEX
    URBANOS, F
    HALCROW, MA
    FERNANDEZBAEZA, J
    DAHAN, F
    LABROUE, D
    CHAUDRET, B
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) : 3484 - 3493
  • [39] Rh(III)-Catalyzed Double C-H Functionalization of Indoles with Cyclopropenones via Sequential C-H/C-C/C-H Bond Activation
    Zhang, Yan-Bo
    Li, Bin-Shi
    Xu, Guo-Jie
    Sun, Wei
    Sun, Meng
    ORGANIC LETTERS, 2023, 25 (21) : 3922 - 3926
  • [40] Carbon Monoxide Activation by a Molecular Aluminium Imide: C-O Bond Cleavage and C-C Bond Formation
    Heilmann, Andreas
    Hicks, Jamie
    Vasko, Petra
    Goicoechea, Jose M.
    Aldridge, Simon
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (12) : 4897 - 4901