Pd-Catalyzed, Ligand-Enabled Stereoselective 1,2-Iodine(III) Shift/ 1,1-Carboxyalkynylation of Alkynylbenziodoxoles

Junliang Wu; Kai Xu; Hajime Hirao; Naohiko Yoshikai

首页> 外文期刊>Chemistry: A European journal >Pd-Catalyzed, Ligand-Enabled Stereoselective 1,2-Iodine(III) Shift/ 1,1-Carboxyalkynylation of Alkynylbenziodoxoles

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Pd-Catalyzed, Ligand-Enabled Stereoselective 1,2-Iodine(III) Shift/ 1,1-Carboxyalkynylation of Alkynylbenziodoxoles

机译：PD催化，支持配体的立体选择1,2-碘（III）换碘苯并苯并苯并苯并氧苯胺化/ 1,1-羧炔酰胺化

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A Pd~(II)-catalyzed 2:1 coupling reaction of alkynylbenziodoxole with carboxylic acid to afford (alk-1-en-3- ynyl)benziodoxole, which is efficiently promoted by an octahydrophenazine ligand, is reported. The reaction involves a Pd-assisted 1,2-iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups (the latter originating from another molecule of the alkynylbenziodoxole) into the 1-position of the transient Pd-vinylidene species. The product of this 1,1-carboxyalkynylation reaction serves as a new functionalized enyne-type building block for further synthetic transformations.

机译：报道了PD〜（II） - 催化2：1炔基苯并辛氧氧唑与羧酸得到的（ALK-1-烯-3-炔基）苯二唑氧唑，其被八氢噻吩嗪配体有效促进的苯二苯甲脂氧脂氧脂。该反应涉及炔基苯并辛氧脂氧脂的PD辅助1,2-碘（III）偏移，然后立体选择性引入羧基和炔基（后者源自炔基苯并辛氧脂氧脂氧脂的另一分子）进入瞬态Pd-亚基二甲苯的1-位物种。该1,1-羧炔酰胺化反应的产物用作新的官能化enyne型构建块，用于进一步的合成转变。

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来源
《Chemistry: A European journal》 |2017年第7期|共5页
作者
Junliang Wu; Kai Xu; Hajime Hirao; Naohiko Yoshikai;
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作者单位

Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 (Singapore);

Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 (Singapore);

Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 (Singapore);

Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 (Singapore);

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
alkynylation; carboxylic acid; cross-coupling; hypervalent iodine; palladium;

机译：alkynylation;羧酸;交叉偶联;高效碘;钯;

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专利

1. Pd-Catalyzed, Ligand-Enabled Stereoselective 1,2-Iodine(III) Shift/ 1,1-Carboxyalkynylation of Alkynylbenziodoxoles [J] . Junliang Wu, Kai Xu, Hajime Hirao, Chemistry: A European journal . 2017,第7期

机译：PD催化，支持配体的立体选择1,2-碘（III）换碘苯并苯并苯并苯并氧苯胺化/ 1,1-羧炔酰胺化
2. Modular approach to the synthesis of polydentate NHC-ligand precursors (benzimidazolium salts) containing axial chiral 1,1′-binaphthyl via Pd-catalyzed N-arylation of 1,2-diaminobenzene [J] . ZhuS., WangC., ZhaoS., Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2014,第2期

机译：模块化方法通过Pd催化1,2-二氨基苯的N-芳基化反应合成含有轴向手性1,1'-联萘基的多齿NHC配体前体（苯并咪唑盐）
3. Modular approach to the synthesis of polydentate NHC-ligand precursors (benzimidazolium salts) containing axial chiral 1,1′-binaphthyl via Pd-catalyzed N-arylation of 1,2-diaminobenzene [J] . ZhuS., WangC., ZhaoS., Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2014,第2期

机译：通过PD催化的N-芳基化合物含有轴向手性1,1'-二苯甲基的多弥敦式NHC-配体前体（苯并咪唑鎓盐）合成的模块化方法
4. Iodine(III)-Catalyzed, Enantioselective 1,2-Difluorination of Cinnamamides [D] . Haj, Moriana Khaled. 2020

机译：碘（III） - 催化，对肉桂酰胺的映选择性1,2-二氟化
5. Stereoselective Formation of Substituted 13-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III) [O] . Mio Shimogaki, Morifumi Fujita, Takashi Sugimura 2015

机译：在高价碘（III）氧化烯烃的过程中通过三组分组装立体选择性形成13-二氧戊环
6. Stereoselective Synthesis of Substituted 1,3-Oxazolidines via Pd-Catalyzed Carboamination Reactions ofO-Vinyl-1,2-Amino Alcohols [O] . Amanda F. Ward, John P. Wolfe 2011

机译：通过PD催化的碳化碳化反应O-Vinyl-1,2-氨基醇的立体选择性合成取代的1,3-恶唑啉

Pd-Catalyzed, Ligand-Enabled Stereoselective 1,2-Iodine(III) Shift/ 1,1-Carboxyalkynylation of Alkynylbenziodoxoles

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