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使用吲哚BX类高价碘试剂的铑催化杂芳烃的C-H官能化反应

Rhodium-catalyzed C-H functionalization of heteroarenes using indoleBX hypervalent iodine reagents.

作者信息

Grenet Erwann, Das Ashis, Caramenti Paola, Waser Jérôme

机构信息

Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fedérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.

出版信息

Beilstein J Org Chem. 2018 May 25;14:1208-1214. doi: 10.3762/bjoc.14.102. eCollection 2018.

DOI:10.3762/bjoc.14.102
PMID:29977388
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6009173/
Abstract

The C-H indolation of heteroarenes was realized using the benziodoxolone hypervalent iodine reagents indoleBXs. Functionalization of the C-H bond in bipyridinones and quinoline -oxides catalyzed by a rhodium complex allowed to incorporate indole rings into aza-heteroaromatic compounds. These new transformations displayed complete regioselectivity for the C-6 position of bipyridinones and the C-8 position of quinoline -oxides and tolerated a broad range of functionalities, such as halogens, ethers, or trifluoromethyl groups.

摘要

使用苯并碘杂环酮高价碘试剂吲哚BX实现了杂芳烃的C-H吲哚化反应。铑配合物催化的联吡啶酮和喹啉氧化物中C-H键的官能团化反应能够将吲哚环引入氮杂芳烃化合物中。这些新的转化反应对联吡啶酮的C-6位和喹啉氧化物的C-8位表现出完全的区域选择性，并且能够耐受多种官能团，如卤素、醚或三氟甲基。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/6a1fb97883cb/Beilstein_J_Org_Chem-14-1208-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/bbd01bd19f50/Beilstein_J_Org_Chem-14-1208-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/cbdd127df083/Beilstein_J_Org_Chem-14-1208-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/55d19a0f3a3c/Beilstein_J_Org_Chem-14-1208-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/b3adf18f9047/Beilstein_J_Org_Chem-14-1208-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/6a1fb97883cb/Beilstein_J_Org_Chem-14-1208-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/bbd01bd19f50/Beilstein_J_Org_Chem-14-1208-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/cbdd127df083/Beilstein_J_Org_Chem-14-1208-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/55d19a0f3a3c/Beilstein_J_Org_Chem-14-1208-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/b3adf18f9047/Beilstein_J_Org_Chem-14-1208-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8812/6009173/6a1fb97883cb/Beilstein_J_Org_Chem-14-1208-g006.jpg

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