Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis-Hillman alcohols with propiolic acids: a highly regio- and stereoselective synthesis of 1,5-diarylpent-1-en-4-yne derivatives

Tummanapalli Satyanarayana; Muthuraman Parthasarathy; Vangapandu Dhanunjaya Naidu; Shanmugavel Gnanakalai; Kambampati Sanjeeva; Lee Kee Wei

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Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis-Hillman alcohols with propiolic acids: a highly regio- and stereoselective synthesis of 1,5-diarylpent-1-en-4-yne derivatives

机译：PD催化的乙酸乙酸乙酸乙酸乙酸醇与丙醇酸：1,5-二芳基-1-烯-4-苯乙烯衍生物的高度测定和立体选择合成

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Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis-Hillman alcohols with alkynyl carboxylic acids leading to the formation of an important class of 1,5-diarylpent-1-en-4-ynes in a highly regio- and stereoselective manner has been developed. Decarboxylative coupling happened via an exclusively S(N)2' pathway. Acetates of the Baylis-Hillman alcohols derived from alkyl acrylates, ethyl vinyl ketone and phenyl vinyl sulfone provided exclusively (E)-1,5- diarylpent-1-en-4-ynes while the acetates of the Baylis-Hillman alcohols derived from acrylonitrile provided exclusively (Z)-1,5-diarylpent-1-en-4-ynes.

机译：通过炔基羧酸乙酸盐的乙酸叔羧酸烯醇烯醇烯醇偶联偶联偶氮烯醇烯烯醇烯烯醇偶联偶氮烯基，其以高度的测定和立体选择性方式形成重要的1,5-二芳基-1-EN-4-ynes的形成。脱羧耦合通过A专用的S（n）2'途径发生。衍生自丙烯酸烷基酯，乙基乙烯基酮和苯基乙烯基砜的醋酸醇，仅提供（e）-1,5-二芳酯-1-en-4-ynes，而均丙烯腈衍生的Baylis-Hillman醇的醋酸酯专门提供（Z）-1,5-二芳基 - 1-EN-4-YNES。

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《RSC Advances》 |2015年第61期|共8页
作者
Tummanapalli Satyanarayana; Muthuraman Parthasarathy; Vangapandu Dhanunjaya Naidu; Shanmugavel Gnanakalai; Kambampati Sanjeeva; Lee Kee Wei;
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Albany Mol Res Singapore Res Ctr Singapore 117525 Singapore;

Albany Mol Res Singapore Res Ctr Singapore 117525 Singapore;

Albany Mol Res Singapore Res Ctr Singapore 117525 Singapore;

Albany Mol Res Singapore Res Ctr Singapore 117525 Singapore;

Albany Mol Res Singapore Res Ctr Singapore 117525 Singapore;

Albany Mol Res Singapore Res Ctr Singapore 117525 Singapore;

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1. Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis-Hillman alcohols with propiolic acids: a highly regio- and stereoselective synthesis of 1,5-diarylpent-1-en-4-yne derivatives [J] . Tummanapalli Satyanarayana, Muthuraman Parthasarathy, Vangapandu Dhanunjaya Naidu, RSC Advances . 2015,第61期

机译：PD催化的乙酸乙酸乙酸乙酸乙酸醇与丙醇酸：1,5-二芳基-1-烯-4-苯乙烯衍生物的高度测定和立体选择合成
2. Pd-catalyzed decarboxylative coupling of propiolic acids: One-pot synthesis of 1,4-disubstituted 1,3-diynes via Sonogashira-homocoupling sequence [J] . Park J., Park E., Kim A., The Journal of Organic Chemistry . 2011,第7期

机译：Pd催化的丙酸脱羧偶联：通过Sonogashira-homocoupling序列一锅法合成1,4-二取代的1,3-二炔
3. Palladium-Mediated Highly Regio- and Stereoselective Intermolecular β-Arylation on Allylic Alcohols: Synthesis of Functionalized Allylic Alcohols [J] . J. Krishna, A. Gopi Krishna Reddy, B. Venkat Ramulu, Synlett . 2012,第3期

机译：钯介导的对烯醇的高度区域和立体选择性分子间β-芳基化反应：官能化烯醇的合成
4. Highly Efficient Synthesis of Allenyltitanium Reagents Propargyl Alcohol Derivatives.Practical Synthesis of Homopargyl Alcohols [C] . Fang-Long Yang International symposium for Chinese organic chemists . 2000

机译：高效合成亚甲硝基试剂炔丙醇衍生物。常卤醇的实际合成
5. Approaches to the total synthesis of (+/-)-pseudomonic acids. Model studies and reagent development in stereo- and regiocontrolled Pd-catalyzed alkylations and arylations of allylic alcohol derivatives. [D] . Brescia, Marc-Raleigh. 1997

机译：（+/-）-假单仲酸的全合成方法。立体和区域控制的Pd催化烯丙基醇衍生物的烷基化和芳基化的模型研究和试剂开发。
6. Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling [O] . Chao Wang, Tomas Tobrman, Zhaoqing Xu, -1

机译：通过丙炔Bromoboration和串联钯催化的交叉偶联（Z）三取代烯烃的高度区域选择性和立体选择性合成
7. Palladium-mediated highly regio- and stereoselective intermolecular β-arylation on allylic alcohols: Synthesis of functionalized allylic alcohols [O] . J Krishna, A Gopi Krishna Reddy, B Venkat Ramulu, 2012

机译：钯介导的烯丙基醇上的高度区域和立体选择性分子间β-芳基化反应：官能化烯丙基醇的合成

Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis-Hillman alcohols with propiolic acids: a highly regio- and stereoselective synthesis of 1,5-diarylpent-1-en-4-yne derivatives

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