化学/区域选择性[5+1]环化宝石-二氟亚甲基烯组装氟化2h -铬和二氢喹啉

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-12-03 DOI:10.1002/adsc.202401110

Zhi Zhou, Zhensheng Lin, Ying Cai, Junwei Ye, Kaifeng Chen, Jieni Zheng, Linxin Zhou, Wei Yi

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引用次数: 0

摘要

利用宝石-二氟亚甲基烯作为多用途偶联伙伴，合成了多种含氟2h -铬和二氢喹啉，参与过渡金属催化的2-烯基酚/苯胺级联C-H活化/[5+1]环化反应。该方案具有特定的化学/区域选择性，氧化还原中性方式和良好的相容性，提供了一个直接的合成途径，以吸引氟烯基部分的设备来吸引基序。独特的宝石-二氟效应导致σ碳-金属键的质子裂解，从而解释了通过顺序的碳氢活化/烯插入/质子裂解/环化/β-F消除过程所观察到的选择性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Chemo-/Regioselective [5+1] Annulation with gem-Difluoromethylene Allenes for the Assembly of Fluorinated 2H-Chromenes and Dihydroquinolines

A variety of fluorinated 2H-chromenes and dihydroquinolines was synthesized by virtue of gem-difluoromethylene allenes as versatile coupling partners to participate in the transition metal-catalysed cascade C-H activation/[5+1] annulation of 2-alkenylphenols/anilines. This protocol features specific chemo-/regioselectivity, redox-neutral manner and good compatibility, providing a straightforward synthetic route to intriguing motifs with the equipment of attractive fluoroalkenyl moiety. The distinctive gem-difluorine effect induced an unexpected protonolysis of σ carbon-metal bond, thus accounting for the observed selectivity via sequential C-H activation/allene insertion/protonolysis/cyclization/β-F elimination process.

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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.