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未保护的富氮杂环的铃木-宫浦交叉偶联反应：底物范围及机理研究

Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles: substrate scope and mechanistic investigation.

作者信息

Düfert M Alexander, Billingsley Kelvin L, Buchwald Stephen L

机构信息

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

出版信息

J Am Chem Soc. 2013 Aug 28;135(34):12877-85. doi: 10.1021/ja4064469. Epub 2013 Aug 16.

DOI:10.1021/ja4064469
PMID:23909907
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3807799/
Abstract

The Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles using precatalysts P1 or P2 is reported. The procedure allows for the reaction of variously substituted indazole, benzimidazole, pyrazole, indole, oxindole, and azaindole halides under mild conditions in good to excellent yields. Additionally, the mechanism behind the inhibitory effect of unprotected azoles on Pd-catalyzed cross-coupling reactions is described based on evidence gained through experimental, crystallographic, and theoretical investigations.

摘要

报道了使用预催化剂P1或P2对未保护的富氮杂环进行铃木-宫浦交叉偶联反应。该方法能使各种取代的吲唑、苯并咪唑、吡唑、吲哚、氧化吲哚和氮杂吲哚卤化物在温和条件下以良好至优异的产率发生反应。此外，基于通过实验、晶体学和理论研究获得的证据，描述了未保护的唑类对钯催化交叉偶联反应抑制作用背后的机制。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/fc3a3fa2ae29/nihms517090f14.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/b82c98d5e118/nihms517090f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/972ba4a7e73b/nihms517090f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/313cf72ce447/nihms517090f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/2cc8c7fd357f/nihms517090f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/a7e756ea61da/nihms517090f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/a6c10d4d1bc5/nihms517090f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/70037dc17d59/nihms517090f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/b680a3a6c25f/nihms517090f10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/c7ad83bf5b81/nihms517090f11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/b6a04bee6ff8/nihms517090f12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/38b078094d68/nihms517090f13.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/fc3a3fa2ae29/nihms517090f14.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/bd776b5c4b5b/nihms517090f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/aafa0003bc74/nihms517090f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/b82c98d5e118/nihms517090f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/972ba4a7e73b/nihms517090f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/313cf72ce447/nihms517090f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/2cc8c7fd357f/nihms517090f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/a7e756ea61da/nihms517090f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/a6c10d4d1bc5/nihms517090f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/70037dc17d59/nihms517090f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/b680a3a6c25f/nihms517090f10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/c7ad83bf5b81/nihms517090f11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/b6a04bee6ff8/nihms517090f12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/38b078094d68/nihms517090f13.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e4/3807799/fc3a3fa2ae29/nihms517090f14.jpg

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