高价碘通过Csp2-H / Csp3-H保留双官能团对2 -取代吲哚的1,3碘酯化反应（III）

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-03-04 DOI:10.1002/adsc.202401496

Hiroko Wasaki , Katsuhiko Moriyama

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引用次数: 0

摘要

研究了2取代吲哚与三卤乙酸、碘化试剂和高价碘（III）化合物的1,3‐碘酯化反应，作为酸促进的C<；sub>sp2</sub> -H /C<sub>sp3</sub>； -H双官能化反应，得到3‐碘‐2‐三卤乙酰氧基甲基吲哚。三卤酯基团的一锅1,3碘酯化/水解通过重排pivaloyl得到3 - iodo - 2 - pivaloylmethyl吲哚。在形成吲哚基（甲酰基）三卤乙酸碘后，该反应通过三卤乙酸辅助的亲电活化进行。

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1,3‐Iodoesterification of 2‐Substituted Indoles via Csp2−H/Csp3−H Retained Dual Functionalization Using Hypervalent Iodine(III)

A 1,3‐iodoesterification of 2‐substituted indoles with trihaloacetic acid, iodination reagent, and hypervalent iodine(III) compound was developed as an acid‐promoted C_sp2−H/C_sp3−H dual functionalization reaction to furnish 3‐iodo‐2‐trihaloacetoxymethyl indoles. The one‐pot 1,3‐iodoesterification/hydrolysis of the trihaloester group provided 3‐iodo‐2‐pivaloylmethyl indoles via the rearrangement of the pivaloyl group. The reaction proceeded through a trihaloacetic acid‐assisted electrophilic activation of the iodination reagent after the formation of an indolyl(mesityl)iodonium trihaloacetate.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.