70298-83-8Relevant academic research and scientific papers
Equivalent Loading of Directed Arenes in Pd(II)-Catalyzed Oxidative Cross-Coupling of Aryl C-H Bonds at Room Temperature
Mei, Chong,Zhao, Mengdi,Lu, Wenjun
, p. 2714 - 2733 (2021/02/01)
The unsymmetrical biaryls (Ar1-Ar2) produced by the catalytic cross-couplings of aryl halides (Ar1-halo) with aryl metallics (Ar2-M) in the loading ratio of 1:1 are popular in chemical synthesis. In contrast, there has been less precedence on the same biaryls produced effectively from two normal aryl C-H bonds with equivalent loading. Here, we report that, in a palladium/oxidant/acid catalytic system at room temperature, one arene (Ar1-H, 1 equiv) can highly selectively couple with the other one (Ar2-H, 1 equiv) to afford the target Ar1-Ar2 just by controlling the directing groups and the substituted groups on their phenyl rings. The utility of this one-one cross-coupling is also demonstrated by synthesis of a few bioactive molecules.
Palladium(II)-Catalyzed Oxidative Homo- and Cross-Coupling of Aryl ortho -sp2 C-H Bonds of Anilides at Room Temperature
Mei, Chong,Lu, Wenjun
, p. 4812 - 4823 (2018/04/26)
The preparation of secondary 2,2'-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp2 C-H bonds of anilides in the presence of catalytic Pd(OAc)2 and K2S2O8 as an oxidant in MsOH/CF3CO2H (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions.
Rhodium(III)-catalysed, redox-neutral C(sp2)-H alkenylation using pivalimide as a directing group with internal alkynes
Kathiravan, Subban,Nicholls, Ian A.
supporting information, p. 1 - 4 (2016/12/23)
In the presence of [RhCp?Cl2]2, N-pivaloyl anilines react with internal alkynes to give the corresponding 2-alkenylpivalimides under redox neutral conditions through C-H activation. This redox neutral hydroarylation, which does not require an external organic acid, unlocks a regioselective synthetic route to 2-alkenyl anilines and is generally applicable to diversely substituted electron rich and electron poor pivalimides.
Palladium-Catalysed Synthesis of α-(Trifluoromethyl)styrenes by Means of Directed C-H Bond Functionalization
Zhao, Qun,Besset, Tatiana,Poisson, Thomas,Bouillon, Jean-Philippe,Pannecoucke, Xavier
, p. 76 - 82 (2016/01/26)
We report the first introduction of 2-bromo-3,3,3-trifluoropropene (BTP) by directed C-H bond functionalization. The developed method gives straightforward access to α-(trifluoromethyl)styrene derivatives without prior prefunctionalization of the substrates. This palladium-catalysed transformation was applied to a broad range of substrates, and the corresponding trifluoromethylated products were obtained in good yields. This approach represents an alternative pathway to the classical method previously used to access such molecules.
A highly efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides
Li, Dengke,Xu, Ning,Zhang, Yicheng,Wang, Lei
supporting information, p. 14862 - 14865 (2014/12/11)
An efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides was developed. A variety of anilides reacted with aryl acylperoxides to afford the corresponding ortho-arylation products, and N-methoxyarylamides generated phenanthridinones. This journal is
CuCl-catalyzed ortho trifluoromethylation of arenes and heteroarenes with a pivalamido directing group
Cai, Shangjun,Chen, Chao,Sun, Zelin,Xi, Chanjuan
supporting information, p. 4552 - 4554 (2013/06/04)
The CuCl catalyzed direct trifluoromethylation of sp2 C-H bonds has been realized, using the Togni reagent as the CF3 source. This reaction achieves the goal of regio-selectively converting C-H into C-CF 3 with ecological and readily available starting materials.
Copper-catalyzed dehydrogenative cross-coupling reactions of N-para-tolylamides through successive C-H activation: Synthesis of 4H-3,1-benzoxazines
Xiong, Tao,Li, Yan,Bi, Xihe,Lv, Yunhe,Zhang, Qian
supporting information; experimental part, p. 7140 - 7143 (2011/09/12)
A novel annulation reaction of readily available tolylamides was catalyzed by Cu(OTf)2 in the presence of Selectfluor and water through successive intermolecular C-H activated dehydrogenative cross-coupling reactions of benzylic methyl C(sp3)-H and aromatic C(sp2)-H bonds, and subsequent intramolecular C-O bond formation (see scheme). Copyright
Remote amide-directed palladium-catalyzed benzylic C-H amination with N-fluorobenzenesulfonimide
Xiong, Tao,Li, Yan,Lv, Yunhe,Zhang, Qian
supporting information; experimental part, p. 6831 - 6833 (2010/10/21)
An unprecedented remote amide-directed palladium-catalyzed intermolecular highly selective benzylic C-H amination with N-fluorobenzenesulfonimide is developed, which represents the first direct benzylic C-H amination with a non-nitrene nitrogen source. This methodology provides a novel approach to circumvent the common ortho aromatic C-H selectivity in directed palladium catalyzed C-H functionalization.
Pd-catalyzed intermolecular ortho-C-H amidation of anilides by N-nosyloxycarbamate
Ng, Ka-Ho,Chan, Albert S. C.,Yu, Wing-Yiu
supporting information; body text, p. 12862 - 12864 (2010/11/03)
A palladium-catalyzed ortho-C-H amidation of anilides by N-nosyloxycarbamates was developed for the synthesis of 2-aminoanilines. This reaction can be carried out under relatively mild conditions and exhibits excellent regioselectivity and functional group tolerance. The amidation reaction is probably initiated by rate-limiting C-H cyclopalladation (k H/kD = 3.7) to form an arylpalladium complex, followed by nitrene functionalization.
PREPARATION AND PYROLYSIS OF SUBSTITUTED ETHANOANTHRACENES - A GENERAL SYNTHESIS OF 2,3-DISUBSTITUTED ANTHRACENES
Baldwin, Jack E.,Swanson, Alistair G.,Cha, Jin Kun,Murphy, John A.
, p. 3943 - 3956 (2007/10/02)
9,10-Ethano-9,10-dihydroanthracene has been found functionalised regioselectively to give a range of 2-substituted and 2,3-disubstituted derivatives.Flasch vakuum pyrolysis of these compounds has provided the first general synthesis of 2,3-disubstituted anthracenes.The observed regioselectivity is in accord with the Finnegan-Streitwieser model of the electronic influence of a strained ring fused to an aromatic ring.
