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苄基醚与同位素标记格氏试剂的立体专一性镍催化交叉偶联反应

Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Benzylic Ethers with Isotopically-Labeled Grignard Reagents.

作者信息

Dawson David D, Jarvo Elizabeth R

机构信息

Department of Chemistry, University of California , Irvine, California 92697-2025, United States.

出版信息

Org Process Res Dev. 2015 Oct 16;19(10):1356-1359. doi: 10.1021/acs.oprd.5b00148. Epub 2015 Sep 11.

DOI:10.1021/acs.oprd.5b00148
PMID:27458328
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4955521/
Abstract

In this manuscript we highlight the potential of stereospecific nickel-catalyzed cross-coupling reactions for applications in the pharmaceutical industry. Using an inexpensive and sustainable nickel catalyst, we report a gram-scale Kumada cross-coupling reaction. Reactions are highly stereospecific and proceed with inversion at the benzylic position. We also expand the scope of our reaction to incorporate isotopically labeled substituents.

摘要

在本手稿中，我们强调了立体特异性镍催化交叉偶联反应在制药行业应用中的潜力。使用一种廉价且可持续的镍催化剂，我们报道了克级规模的熊田交叉偶联反应。反应具有高度立体特异性，且在苄基位置发生构型翻转。我们还扩大了反应范围，纳入了同位素标记的取代基。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4c23/4955521/c2e0747d0fb0/op-2015-00148w_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4c23/4955521/7882193b8cbc/op-2015-00148w_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4c23/4955521/383a03cf7303/op-2015-00148w_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4c23/4955521/2646e7109128/op-2015-00148w_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4c23/4955521/c2e0747d0fb0/op-2015-00148w_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4c23/4955521/7882193b8cbc/op-2015-00148w_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4c23/4955521/383a03cf7303/op-2015-00148w_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4c23/4955521/2646e7109128/op-2015-00148w_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4c23/4955521/c2e0747d0fb0/op-2015-00148w_0006.jpg

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