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对映体特异性的、镍催化的新戊酸烯丙酯与芳基硼酸酯的交叉偶联反应。

Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines.

作者信息

Srinivas Harathi D, Zhou Qi, Watson Mary P

机构信息

Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.

出版信息

Org Lett. 2014 Jul 3;16(13):3596-9. doi: 10.1021/ol5016724. Epub 2014 Jun 13.

DOI:10.1021/ol5016724
PMID:24927013
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4084837/
Abstract

We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.

摘要

我们已经开发出一种对映体特异性的、镍催化的不对称1,3-二取代烯丙基新戊酸酯与芳基硼酸酯的交叉偶联反应。该反应的成功依赖于使用BnPPh2作为镍(0)催化剂的辅助配体以及使用甲氧基钠作为碱。此方法在烯丙基新戊酸酯和芳基硼酸酯中均表现出优异的官能团耐受性和广泛的适用范围,能够以高收率制备1,3-二芳基烯丙基产物,且具有出色的区域选择性和立体化学保真度。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/0e9ab46f508f/ol-2014-016724_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/9e0ccfb27e66/ol-2014-016724_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/7c13c5995b7e/ol-2014-016724_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/a4d328ed694e/ol-2014-016724_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/305fc9538bd4/ol-2014-016724_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/0e9ab46f508f/ol-2014-016724_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/9e0ccfb27e66/ol-2014-016724_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/7c13c5995b7e/ol-2014-016724_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/a4d328ed694e/ol-2014-016724_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/305fc9538bd4/ol-2014-016724_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be40/4084837/0e9ab46f508f/ol-2014-016724_0007.jpg

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