Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes

Rout Laxmidhar; Parida Bibhuti Bhusan; Florent Jean-Claude; Johannes Ludger; Choudhury Santosh Kumar; Phaomei Ganngam; Scanlon Joe; Bertounesque Emmanuel

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Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes

机译：芳基乙炔的C（sp）-H键的无金属活化

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C(sp)-H Bond activation of acetylene molecule still remains a challenge for synthetic organic chemists. In practice, acetylenes are activated by strong bases and metals. The first example for activating acetylenic protons under base and metal-free conditions is reported here. It involves a general method for synthesizing propargylic derivatives of cotarnine. An array of tetrahydroisoquinolines alkaloids was synthesized by C(sp)-H bond activation of aromatic acetylenes with cotarnine at room temperature. A DFT-based mechanism is proposed for the reaction.

机译：乙炔分子的C（sp）-H键活化对于合成有机化学家仍然是一个挑战。实际上，乙炔被强碱和金属活化。这里报道了在无碱和无金属条件下活化炔属质子的第一个例子。它涉及合成烟碱的炔丙基衍生物的一般方法。四氢异喹啉类生物碱的阵列是通过在室温下用烟熏碱对芳族乙炔进行C（sp）-H键活化而合成的。提出了基于DFT的反应机理。

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《Chemistry: A European journal》 |2016年第42期|共4页
作者
Rout Laxmidhar; Parida Bibhuti Bhusan; Florent Jean-Claude; Johannes Ludger; Choudhury Santosh Kumar; Phaomei Ganngam; Scanlon Joe; Bertounesque Emmanuel;
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正文语种 eng
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alkaloid; cotarnine; density functional calculations; isoquinoline; phenylacetylene;

机译：生物碱;烟碱;密度泛函;异喹啉;苯乙炔;

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1. Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes [J] . Rout Laxmidhar, Parida Bibhuti Bhusan, Florent Jean-Claude, Chemistry: A European journal . 2016,第42期

机译：芳基乙炔的C（sp）-H键的无金属活化
2. Intermolecular Oxidative C-N Bond Formation under Metal-Free Conditions: Control of Chemoselectivity between Aryl sp~2 and Benzylic sp~3 C-H Bond Imidation [J] . Hyun Jin Kim, Jiyu Kim, Seung Hwan Cho, Journal of the American Chemical Society . 2011,第41期

机译：无金属条件下分子间氧化性C-N键的形成：控制芳基sp〜2与苯甲酰sp〜3的C-H键酰胺化反应的化学选择性
3. Effects of aryl and arylethynyl substituents at the 1-position on rotational barrier around C(sp)-C9sp~3) bonds and bending deformation of acetylenic carbons in bis(9-triptycyl)ethynes [J] . Shinji Toyota, Takao Yamamori, Toshiaki Makino Tetrahedron . 2001,第17期

机译：1-位芳基和芳基乙炔基取代基对C（sp）-C9sp〜3）键周围的旋转势垒和双（9-三苯甲基）乙炔炔烃弯曲变形的影响
4. Ph3 P-Mediated Synthesis of Functionalized 3-(Aryl)-1-phenyl-lif-pyrazoles from 1-ChIoro(aryl)methylene-2-phenylhydrazines and Activated Acetylenes??? [C] . European Symposium on Organic Chemistry . 2009

机译：pH3介导的官能化3-（芳基）-1-苯基 - LiF-吡唑的合成1- Chioro（芳基）亚甲基 -2-苯基肼和活化乙炔（乙炔）--??
5. Part I: Asymmetric synthesis of alpha-allyl-alpha-aryl alpha-amino acids. Part II: Asymmetric spirocyclization of allenyl ketones. Part III: Chemoselective activation of C(sp3)--H bond over C(sp 2)--H bond with Pd(II). [D] . Curto, John M. 2014

机译：第一部分：α-烯丙基-α-芳基α-氨基酸的不对称合成。第二部分：烯基酮的不对称螺环化。第三部分：与Pd（II）相比，C（sp3）-H键的化学选择性活化。
6. Metal-Free Preparation of Cycloalkyl Aryl Sulfides via Di-tert-butylPeroxide-Promoted Oxidative C(sp3)BONDH Bond Thiolation ofCycloalkanes [O] . Jincan Zhao, Hong Fang, Jianlin Han, -1

机译：二叔丁基无金属制备环烷基芳基硫醚过氧化物促进的氧化型C（sp3）BOND H键硫醇化环烷烃
7. Redox-Activated Amines in C(sp3)C(sp) and C(sp3)C(sp2) Bond Formation Enabled by Metal-Free Photoredox Catalysis [O] . -1

机译：C（SP3）C（SP）和C（SP3）C（SP2）C（SP2）键合的氧化还原活性胺（SP3）C（SP2）键合形成

Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes

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