Expanding the Scope of the Tail-to-Tail Dimerization of Vinyl Compounds Catalyzed by N-Heterocyclic Carbene

Matsuoka Shin-ichi; Nakazawa Masanori; Suzuki Masato

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Expanding the Scope of the Tail-to-Tail Dimerization of Vinyl Compounds Catalyzed by N-Heterocyclic Carbene

机译：扩大由N-杂环基石催化的乙烯基化合物的尾尾二聚化的范围

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The tail-to-tail dimerization of vinyl compounds catalyzed by an N-heterocyclic carbene was found to show a very broad substrate scope and tolerance to various functional groups. The optimization of the dimerizations of 2-vinylpyridine and n-butyl acrylate, as low and high electrophilicity model substrates, indicates that high reaction temperatures around 150 degrees C are required for both substrates. In addition to methacrylates and methacrylonitrile, the applicable substrates range from an activated styrene and vinyl pyridines to highly reactive acrylonitrile, dimethyl acrylamide, and various functionalized acrylates. The alcohol additives significantly increase the catalytic turnover number to 18 for the dimerization of acrylates. Deuterium labeling experiments indicate that the alcohols promote the intermolecular proton transfers.

机译：发现由N-杂环基石催化的乙烯基化合物的尾尾缩二化，以显示出非常宽的基底范围和对各种官能团的耐受性。优化2-乙烯基吡啶和丙烯酸正丁酯，如低亲电性模型底物的二化表明两个基板需要高反应温度约为150℃。除了甲基丙烯酸酯和甲基丙烯腈之外，适用的基材范围包括活化苯乙烯和乙烯基吡啶，高反应性丙烯腈，二甲基丙烯酰胺和各种官能化丙烯酸酯。醇添加剂显着增加丙烯酸酯二聚化的催化转换数至18。氘标记实验表明醇促进分子间质子转移。

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《Bulletin of the Chemical Society of Japan》 |2015年第8期|共7页
作者
Matsuoka Shin-ichi; Nakazawa Masanori; Suzuki Masato;
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作者单位

Nagoya Inst Technol Grad Sch Engn Dept Mat Sci &

Engn Showa Ku Nagoya Aichi 4668555 Japan;

Nagoya Inst Technol Grad Sch Engn Dept Mat Sci &

Engn Showa Ku Nagoya Aichi 4668555 Japan;

Nagoya Inst Technol Grad Sch Engn Dept Mat Sci &

Engn Showa Ku Nagoya Aichi 4668555 Japan;

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正文语种 eng
中图分类化学;
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1. Expanding the Scope of the Tail-to-Tail Dimerization of Vinyl Compounds Catalyzed by N-Heterocyclic Carbene [J] . Matsuoka Shin-ichi, Nakazawa Masanori, Suzuki Masato Bulletin of the Chemical Society of Japan . 2015,第8期

机译：扩大由N-杂环基石催化的乙烯基化合物的尾尾二聚化的范围
2. Tail-to-tail dimerization and Rauhut-Currier reaction of disubstituted Michael acceptors catalyzed by N-heterocyclic carbene [J] . Matsuoka Shin-ichi, Awano Naoki, Nakazawa Masanori, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2016,第50期

机译：N-杂环卡宾催化的双取代Michael受体的尾到尾二聚和Rauhut-Currier反应
3. Experimental mechanistic studies of the tail-to-tail dimerization of methyl methacrylate catalyzed by N-heterocyclic carbene [J] . Kato T., Ota Y., Matsuoka S.-I., The Journal of Organic Chemistry . 2013,第17期

机译：N-杂环卡宾催化甲基丙烯酸甲酯的尾到尾二聚反应的实验机理研究
4. Controlled Radical Polymerization of Vinyl Monomers Catalyzed by Ruthenium N-Heterocyclic Carbene Complexes [C] . Sebastien Delfosse, Aurore Richel, Lionel Delaude, American Chemical Society . 2006

机译：钌N-杂环碳烯络合物催化的乙烯基单体的控制自由基聚合
5. N-heterocyclic carbene catalysis: Expansion of substrate scope and synthesis of electronically diverse tetraaryl N-heterocyclic imidazolium carbene ligands [D] . Ogle, James William 2008

机译：N-杂环卡宾催化：扩大底物范围并合成电子多样性的四芳基N-杂环咪唑鎓卡宾配体
6. N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones [O] . Roxanne L. Atienza, Howard S. Roth, Karl A. Scheidt -1

机译：乙烯基砜的N-杂环卡宾 - 催化的重排
7. α′-Hydroxyenones as Mechanistic Probes and Scope-Expanding Surrogates for α,β-Unsaturated Aldehydes in N-Heterocyclic Carbene-Catalyzed Reactions [O] . Pei-Chen Chiang, Michael Rommel, Jeffrey W. Bode 2009

机译：α'-羟基酮作为机械探针和范围扩张α，β-不饱和醛在N-杂环上催化反应中的α，β-不饱和醛

Expanding the Scope of the Tail-to-Tail Dimerization of Vinyl Compounds Catalyzed by N-Heterocyclic Carbene

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