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双可见光光氧化还原与金催化的芳基化扩环反应

Dual visible light photoredox and gold-catalyzed arylative ring expansion.

作者信息

Shu Xing-zhong, Zhang Miao, He Ying, Frei Heinz, Toste F Dean

机构信息

Department of Chemistry, University of California , Berkeley, California 94720, United States.

出版信息

J Am Chem Soc. 2014 Apr 23;136(16):5844-7. doi: 10.1021/ja500716j. Epub 2014 Apr 14.

DOI:10.1021/ja500716j
PMID:24730447
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4333587/
Abstract

A combination of visible light photocatalysis and gold catalysis is applied to a ring expansion-oxidative arylation reaction. The reaction provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts. A mechanism involving generation of an electrophilic gold(III)-aryl intermediate is proposed on the basis of mechanistic studies, including time-resolved FT-IR spectroscopy.

摘要

可见光光催化与金催化相结合应用于扩环-氧化芳基化反应。该反应通过烯基和联烯基环烷醇与芳基重氮盐的偶联反应,提供了一种合成官能化环酮的方法。基于包括时间分辨傅里叶变换红外光谱在内的机理研究,提出了一种涉及亲电金(III)-芳基中间体生成的机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5894/4333587/2a12fb8127e1/ja-2014-00716j_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5894/4333587/7e1095619d72/ja-2014-00716j_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5894/4333587/21d618f442bb/ja-2014-00716j_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5894/4333587/2a12fb8127e1/ja-2014-00716j_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5894/4333587/7e1095619d72/ja-2014-00716j_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5894/4333587/21d618f442bb/ja-2014-00716j_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5894/4333587/2a12fb8127e1/ja-2014-00716j_0004.jpg

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