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通过钯-钯金属转移棱镜设计均相无铜Sonogashira反应。

Designing Homogeneous Copper-Free Sonogashira Reaction through a Prism of Pd-Pd Transmetalation.

作者信息

Martek Bruno A, Gazvoda Martin, Urankar Damijana, Košmrlj Janez

机构信息

Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia.

出版信息

Org Lett. 2020 Jul 2;22(13):4938-4943. doi: 10.1021/acs.orglett.0c01227. Epub 2020 May 7.

DOI:10.1021/acs.orglett.0c01227
PMID:32379458
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7341530/
Abstract

Simultaneous introduction of two different palladium (pre)catalysts, one tuned to promote oxidative addition to (hetero)aryl bromide and another to activate terminal alkyne substrate, leads to productive Pd-Pd transmetalation, subsequent reductive elimination, and formation of disubstituted alkyne. This conceptually novel rational design of copper-free Sonogashira reaction enabled facile identification of the reaction conditions, suitable for the synthesis of alkyl, aryl, and heteroaryl substituted alkynes at room temperature with as low as 0.125 mol % total Pd loading.

摘要

同时引入两种不同的钯（预）催化剂，一种用于促进与（杂）芳基溴的氧化加成，另一种用于活化末端炔烃底物，会导致有效的钯-钯转金属化、随后的还原消除，并形成二取代炔烃。这种从概念上讲新颖的无铜Sonogashira反应的合理设计，使得能够轻松确定反应条件，该条件适用于在室温下以低至0.125 mol%的总钯负载量合成烷基、芳基和杂芳基取代的炔烃。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/c9c6b3c97884/ol0c01227_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/4cade1a82d67/ol0c01227_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/c81ce37d791c/ol0c01227_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/86d3472ed656/ol0c01227_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/12a44b372456/ol0c01227_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/6108331074e9/ol0c01227_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/c9c6b3c97884/ol0c01227_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/4cade1a82d67/ol0c01227_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/c81ce37d791c/ol0c01227_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/86d3472ed656/ol0c01227_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/12a44b372456/ol0c01227_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/6108331074e9/ol0c01227_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/59c3/7341530/c9c6b3c97884/ol0c01227_0006.jpg

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