Stereospecific Pd-Catalyzed Intermolecular C(sp(3))-C(sp) Cross-Coupling of Diarylmethyl Carbonates and Terminal Alkynes Under Base-Free Conditions

Tabuchi Sho; Hirano Koji; Miura Masahiro

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Stereospecific Pd-Catalyzed Intermolecular C(sp(3))-C(sp) Cross-Coupling of Diarylmethyl Carbonates and Terminal Alkynes Under Base-Free Conditions

机译：无碱条件下碳酸二芳基甲基酯和末端炔烃的立体定向钯催化分子间C（sp（3））-C（sp）交叉偶联

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摘要

A palladium-catalyzed intermolecular decarboxylative C(sp(3))-C(sp) coupling of diarylmethyl carbonates and terminal alkynes has been developed. The reaction proceeds smoothly under external base-free conditions to deliver the corresponding alkynylated diarylmethanes with the liberation of CO2 and MeOH as the sole byproducts. Moreover, enantioenriched diarylmethyl carbonates are stereospecifically converted to optically active cross-coupling products with inversion of configuration. Thus, the stereospecific palladium catalysis can provide new and unique access to the alkynylated chiral tertiary stereocenters, which are relatively difficult to construct by conventional methods.

机译：已经开发了碳酸二芳基甲基酯和末端炔烃的钯催化的分子间脱羧C（sp（3））-C（sp）偶联。反应在外部无碱条件下平稳进行，以释放相应的炔基化二芳基甲烷，同时释放出CO2和MeOH作为唯一的副产物。此外，对映体富集的碳酸二芳基甲基酯被立体定向转化为旋光性交叉偶联产物，其构型反转。因此，立体有选择性的钯催化可以提供新的和独特的途径来炔化手性叔立体中心，这是相对难以通过常规方法构建的。

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《Chemistry: A European journal》 |2015年第47期|共5页
作者
Tabuchi Sho; Hirano Koji; Miura Masahiro;
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正文语种 eng
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关键词
carbonates; cross-coupling; decarboxylative coupling; palladium; stereospecificity;

机译：碳酸盐;交叉偶联;脱羧偶联;钯;立体特异性;

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1. Stereospecific Pd-Catalyzed Intermolecular C(sp(3))-C(sp) Cross-Coupling of Diarylmethyl Carbonates and Terminal Alkynes Under Base-Free Conditions [J] . Tabuchi Sho, Hirano Koji, Miura Masahiro Chemistry: A European journal . 2015,第47期

机译：无碱条件下碳酸二芳基甲基酯和末端炔烃的立体定向钯催化分子间C（sp（3））-C（sp）交叉偶联
2. Multimetallic catalysed radical oxidative C(sp3)–H/C(sp)–H cross-coupling between unactivated alkanes and terminal alkynes [J] . Shan Tang, Pan Wang, Haoran Li, Nature Communications . 2016,第1期

机译：未活化烷烃与末端炔烃之间多金属催化的自由基氧化C（sp 3 ）– H / C（sp）–H交叉偶联
3. Copper(I)-Catalysed Deacetylenative Cross-Coupling Reaction of Terminal Alkynes with Propargylic Amines via C(sp)–C(sp~3) Bond Cleavage [J] . Yongeun Kim, Hiroyuki Nakamura Synlett . 2012,第11期

机译：铜（I）通过C（sp）–C（sp〜3）键断裂催化末端炔烃与炔丙基胺的脱乙酰化交叉偶联反应
4. Ni/Co-Catalyzed C(sp~3)-C(sp~3) Cross-Coupling Using Alkyl Tosylates as Radical Sources [C] . Takuya Michiyuki, Itaru Osaka, Kimihiro Komeyama 日本化学会春季年会講演予稿集 . 2018

机译：Ni /助催化的C（SP〜3）-C（SP〜3）使用烷基甲磺酸盐作为自由基来源的交叉偶联
5. Transition Metal-Catalyzed Alkyl-Alkyl (sp3-sp3) Cross-Coupling, Its Applications in the Chemistry of N-Boc-Pyrrolidine and Piperidine, and NMR Structural Studies of Organolithiums in Solution. [D] . Tyree, William Stuart. 2011

机译：过渡金属催化的烷基-烷基（sp3-sp3）交叉偶联，在N-Boc-吡咯烷和哌啶的化学中的应用，以及溶液中有机锂的NMR结构研究。
6. Multimetallic catalysed radical oxidative C(sp3)–H/C(sp)–H cross-coupling between unactivated alkanes and terminal alkynes [O] . Shan Tang, Pan Wang, Haoran Li, -1

机译：未活化烷烃与末端炔烃之间的多金属催化自由基氧化C（sp3）–H / C（sp）–H交叉偶联
7. Multimetallic catalysed radical oxidative C(sp3)–H/C(sp)–H cross-coupling between unactivated alkanes and terminal alkynes [O] . Shan Tang, Pan Wang, Haoran Li, 2016

机译：多金属催化的自由基氧化 - C（SP3）-H / C（SP）-H在未激活的烷烃与炔醇末端之间的交叉偶联

Stereospecific Pd-Catalyzed Intermolecular C(sp(3))-C(sp) Cross-Coupling of Diarylmethyl Carbonates and Terminal Alkynes Under Base-Free Conditions

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