Cp*Ir-Catalyzed Acceptorless Dehydrogenation of Carbon-Carbon Single Bonds

被引:18
作者
Ando, Hideaki [1 ]
Kusumoto, Shuhei [1 ]
Wu, Weiwei [2 ]
Nozaki, Kyoko [1 ]
机构
[1] Univ Tokyo, Dept Chem & Biotechnol, Grad Sch Engn, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1138656, Japan
[2] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
FUNCTIONAL BIPYRIDONATE LIGAND; IRIDIUM COMPLEXES; FORMIC-ACID; H ACTIVATION; SATURATED-HYDROCARBONS; TRANSFER HYDROGENATION; NITROGEN-HETEROCYCLES; SECONDARY ALCOHOLS; AQUEOUS-MEDIA; BEARING;
D O I
10.1021/acs.organomet.7b00245
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Tentainethylcyclopentadienyl (Cp*) iridium (III) chloride catalyzed acceptorless dehydrogenation of alpha-tetralone is, reported. Cp* iridium chloride showed higher activity in comparison to other Cp* iridium complexes having bromide, iodide, or,hydride or complexes without a Cp ring. The desired product, naphthol, was obtained in up to 71% yield from alpha-tetralone. The dehydrogenation IT Cp* iridium catalyst could be applied to not only alpha-tetralone but also dihydrocoumarin, dihydroquinolinone, dimethylcyclohexanone, dihydrobenzofuran and 1-isochromanone, although the conversion stayed moderate. The catalytic turnover was, not limited by the increased concentration of the product but by catalyst decomposition.
引用
收藏
页码:2317 / 2322
页数:6
相关论文
共 50 条
[21]   Unusual Carbon-Carbon Bond Formations between Allylboronates and Acetals or Ketals Catalyzed by a Peculiar Indium(I) Lewis Acid [J].
Schneider, Uwe ;
Dao, Hai T. ;
Kobayashi, Shu .
ORGANIC LETTERS, 2010, 12 (11) :2488-2491
[22]   Carbon-Carbon Bond Forming Reactions in Diazines via Transition-Metal-Catalyzed C-H Bond Activation [J].
Gramage-Doria, Rafael ;
Bruneau, Christian .
SYNTHESIS-STUTTGART, 2023, 55 (21) :3470-3486
[23]   Direct conversion of glycerol into formic acid via water stable Pd(II) catalyzed oxidative carbon-carbon bond cleavage [J].
Pullanikat, Prasanna ;
Lee, Joo Ho ;
Yoo, Kyung Soo ;
Jung, Kyung Woon .
TETRAHEDRON LETTERS, 2013, 54 (33) :4463-4466
[24]   Iodide-Ion-Catalyzed Carbon-Carbon Bond-Forming Cross-Dehydrogenative Coupling for the Synthesis of Indole Derivatives [J].
Jia, Zhenhua ;
Nagano, Takashi ;
Li, Xingshu ;
Chan, Albert S. C. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (05) :858-861
[25]   Synthesis of a-Alkylated Ketones via Tandem Acceptorless Dehydrogenation/a-Alkylation from Secondary and Primary Alcohols Catalyzed by Metal-Ligand Bifunctional Iridium Complex [Cp*Ir(2,2′-bpyO)(H2O)] [J].
Wang, Rongzhou ;
Ma, Juan ;
Li, Feng .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) :10769-10776
[26]   Acceptorless dehydrogenative condensation of o-aminobenzamides with aldehydes to quinazolinones in water catalyzed by a watersoluble iridium complex [Cp*Ir(H2O)3][OTf]2 [J].
Li, Feng ;
Lu, Lei ;
Ma, Juan .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (12) :1589-1597
[27]   Palladium Nanoparticles Stabilized by Metal-Carbon Covalent Bonds as an Expeditious Catalyst for the Oxidative Dehydrogenation of Nitrogen Heterocycles [J].
Sun, Xiao-Tao ;
Zhu, Jie ;
Xia, Yun-Tao ;
Wu, Lei .
CHEMCATCHEM, 2017, 9 (13) :2463-2466
[28]   DFT Probe into the Mechanism of Formic Acid Dehydrogenation Catalyzed by Cp*Co, Cp*Rh, and Cp*Ir Catalysts with 4,4′-Amino-/Alkylamino-Functionalized 2,2′-Bipyridine Ligands [J].
Britto, Neethinathan Johnee ;
Jaccob, Madhavan .
JOURNAL OF PHYSICAL CHEMISTRY A, 2021, 125 (43) :9478-9488
[29]   Palladium-catalyzed highly regio- and stereoselective carbon-carbon bond formation reaction of γ-substituted vinylaziridines with a silylated masked acyl cyanide reagent [J].
Kawamura, Tomoyuki ;
Matsu, Nanae ;
Yamauchi, Daisuke ;
Tanabe, Yoo ;
Nemoto, Hisao .
TETRAHEDRON, 2013, 69 (26) :5331-5341
[30]   CuI/H2/NaOH-Catalyzed Cross-Coupling of Two Different Alcohols for Carbon-Carbon Bond Formation: "Borrowing Hydrogen"? [J].
Miura, Takashi ;
Kose, Osamu ;
Li, Feng ;
Kai, Sun ;
Saito, Susumu .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (40) :11146-11151