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铑（III）催化的2-烯基苯酚与炔烃的去芳构化（3+2）环化反应

Rhodium(III)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes.

作者信息

Seoane Andrés, Casanova Noelia, Quiñones Noelia, Mascareñas José L, Gulías Moisés

机构信息

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela , 15782 Santiago de Compostela, Spain.

出版信息

J Am Chem Soc. 2014 May 28;136(21):7607-10. doi: 10.1021/ja5034952. Epub 2014 May 19.

DOI:10.1021/ja5034952
PMID:24820195
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4077242/
Abstract

Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity.

摘要

适当取代的2-烯基苯酚在铑(III)催化剂和氧化剂处理下，能与炔烃发生温和的形式上的[3C+2C]环加成反应。该反应涉及烯基部分末端C-H键的断裂和苯酚环的去芳构化，为构建极具吸引力的螺环骨架提供了一种通用且高效的方法，并且具有高选择性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/e45306d016c2/ja-2014-034952_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/50244d181218/ja-2014-034952_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/7038991be6b7/ja-2014-034952_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/a5f1793987da/ja-2014-034952_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/6861c36c08e0/ja-2014-034952_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/423feaa4fe68/ja-2014-034952_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/64805886f467/ja-2014-034952_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/e45306d016c2/ja-2014-034952_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/50244d181218/ja-2014-034952_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/7038991be6b7/ja-2014-034952_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/a5f1793987da/ja-2014-034952_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/6861c36c08e0/ja-2014-034952_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/423feaa4fe68/ja-2014-034952_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/64805886f467/ja-2014-034952_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14f7/4304480/e45306d016c2/ja-2014-034952_0007.jpg

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