携带1,4-二醚基序的Janus全顺式四氟环己烷的合成

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2024-11-27 DOI:10.1021/acs.joc.4c0234510.1021/acs.joc.4c02345

Thomas J. Poskin, Bruno A. Piscelli, Aidan P. McKay, David B. Cordes, Yuto Eguchi, Shigeyuki Yamada, Rodrigo A. Cormanich* and David O’Hagan*,

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引用次数: 0

摘要

研究了烷基氧化物在五氟芳基醚上的亲核芳香取代（SNAr），这是合成全顺式2,3,5,6-四氟环己基-1,4-二烷基醚的第一步。从实验和理论两方面探讨了SNAr反应，以使邻位/对位/元选择性合理化。叔丁基脱保护后的苯酚烷基化为合成带来了多功能性。Rh(CAAC) 3催化中间四氟芳基-1,4-二醚的芳基加氢步骤生成环己烷产物1。本化学介绍了一类新的Janus氟环己烷衍生物，其醚取代基彼此放置1,4-。

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Synthesis of Janus All-Cis Tetrafluorocyclohexanes Carrying 1,4-Diether Motifs

Nucleophilic aromatic substitutions (S_NAr) of alkoxides on pentafluoroaryl ethers are explored as a first step in a synthesis sequence to generate all-cis 2,3,5,6-tetrafluorocyclohexyl-1,4-dialkyl ethers 1. The S_NAr reaction was explored both experimentally and theoretically to rationalize ortho/para/meta selectivities. tert-Butyl deprotection of products followed by phenol alkylations introduces versatility to the synthesis. The final Rh(CAAC) 3 catalyzed aryl hydrogenation step of intermediate tetrafluoroaryl-1,4-diethers generated cyclohexane products 1. This chemistry introduces a new class of Janus fluorocyclohexane derivatives with ether substituents placed 1,4- to each other.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.