Highly Selective Synthesis of 1,3-Enynes, Pyrroles, and Furans by Manganese(I)-Catalyzed C-H Activation

Cembellin Sara; Dalton Toryn; Pinkert Tobias; Schaefers Felix; Glorius Frank

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Highly Selective Synthesis of 1,3-Enynes, Pyrroles, and Furans by Manganese(I)-Catalyzed C-H Activation

机译：通过锰（I）的1,3- inynes，Pyrololes和Furans的高度选择性合成 - 催化C-H激活

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摘要

A highly selective Mn(I)-catalyzed alkenylation of arenes and heteroarenes with 1,3-diynes is described. The reported transformation overcomes regio-, chemo-, and stereoselectivity challenges associated with the use of these coupling partners. Both symmetrical and unsymmetrical diynes can be applied in this protocol, affording single isomers not only in the synthesis of 1,3-enynes but also in the one-step preparation of pyrroles and furans. This simple strategy features wide functional group tolerance, good reproducibility, and preparative scale utility. The manganese catalyst plays a crucial role in this C-H activation protocol, enabling high selectivity with previously challenging internal alkynes. Furthermore, the synthetic value of the method is highlighted by diverse postsynthesis functionalizations of the final products.

机译：描述了一种高精度的Mn（I） - 催化和杂烷基化合物和用1,3-亚γ的杂烯化酶。报告的转型克服了与使用这些偶联合作伙伴相关的Regio-，Chemo-，和立体选择性挑战。对称和不对称的DIγ可以应用于该方案，其不仅可以在1,3- inynes的合成中提供单一异构体，而且在1,3- inynes的合成中，还可以在吡咯和呋喃的一步制备中。这种简单的策略具有宽功能群体公差，再现性良好和准备比例效用。锰催化剂在该C-H激活方案中起着至关重要的作用，使得能够与先前具有挑战性的内部alkynes具有高选择性。此外，该方法的合成值是通过最终产品的多样性后函数官能化突出的。

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《ACS catalysis》 |2020年第1期|共6页
作者
Cembellin Sara; Dalton Toryn; Pinkert Tobias; Schaefers Felix; Glorius Frank;
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作者单位

Westfalische Wilhelms Univ Munster Organ Chem Inst Corrensstr 40 D-48149 Munster Germany;

Westfalische Wilhelms Univ Munster Organ Chem Inst Corrensstr 40 D-48149 Munster Germany;

Westfalische Wilhelms Univ Munster Organ Chem Inst Corrensstr 40 D-48149 Munster Germany;

Westfalische Wilhelms Univ Munster Organ Chem Inst Corrensstr 40 D-48149 Munster Germany;

Westfalische Wilhelms Univ Munster Organ Chem Inst Corrensstr 40 D-48149 Munster Germany;

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原文格式 PDF
正文语种 eng
中图分类物理化学（理论化学）、化学物理学;
关键词
C-H activation; 1; 3-enynes; 1; 3-diynes; regioselective insertion; heterocycle synthesis;

机译：C-H激活;1;3-inynes;1;3-迪伊斯;区域选择性插入;杂环合成;

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1. Highly Selective Synthesis of 1,3-Enynes, Pyrroles, and Furans by Manganese(I)-Catalyzed C-H Activation [J] . Cembellin Sara, Dalton Toryn, Pinkert Tobias, ACS catalysis . 2020,第1期

机译：通过锰（I）的1,3- inynes，Pyrololes和Furans的高度选择性合成 - 催化C-H激活
2. Arylation/Intramolecular Conjugate Addition of 1,6-Enynes Enabled by Manganese(I)-Catalyzed C-H Bond Activation [J] . Tan Yun-Xuan, Liu Xing-Yu, Zhao Yi-Shuang, Organic letters . 2019,第1期

机译：芳基化/分子内缀合物加入1,6-烯醇的加入锰（I） - 催化的C-H键活化
3. Iridium/Chiral Diene-Catalyzed Enantioselective (3+2) Annulation of Aromatic Ketimines with 1,3-Enynes via C-H Activation [J] . Nagamoto Midori, Sakamoto Kana, Nishimura Takahiro Advanced synthesis & catalysis . 2018,第4期

机译：铱/手性二烯 - 催化芳香酮丙氨酸的映选择性（3 + 2）用C-H激活用1,3- inyn
4. Palladium-catalyzed Selective Arylation of Azulenes at the1,3-Positions based on the C-H Activation by Utilizing 2-PyridylSubstituent as a Directing group [C] . Takuya Nagasawa, Yoshihiro Ogasawara, Tomoaki Yatsu 日本化学会春季年会 . 2020

机译：通过利用2-吡啶基取代剂作为指导基团，基于C-H激活在1,3-位蛋白催化紫红素的选择性浓缩
5. Synthesis of pyrroles, indolizines, and furans via metal-catalyzed cycloisomerization approaches. [D] . Sromek, Anna W. 2005

机译：通过金属催化的环异构化方法合成吡咯，吲哚嗪和呋喃。
6. Rhodium(III)-Catalyzed Alkenyl C-H Bond Functionalization for the Convergent Synthesis of Furans and Pyrroles [O] . Yajing Lian, Tatjana Huber, Kevin D. Hesp, -1

机译：铑（III） - 催化链烯基C-H键官能化用于呋喃和胃肠杆菌的收敛合成
7. Synthesis of Highly Substituted 2,3-Dihydro-1H-pyrrole Derivatives via a Tandem Regioselective Addition of Nitrones to 1,3-Enynes with Subsequent Rearrangement [O] . -1

机译：通过串联区域加入硝酸盐的硝酸盐合成高度取代的2,3-二氢-1H-吡咯衍生物，并随后重排

Highly Selective Synthesis of 1,3-Enynes, Pyrroles, and Furans by Manganese(I)-Catalyzed C-H Activation

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