Preparation of naphthalenes via Pd-catalyzed annulation of 5-(2-bromophenyl)pent-3-en-1-ynes under Suzuki-Miyaura coupling conditions

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2024-08-22 DOI:10.1002/jccs.202400215

Cheng-Kai Hsu, Yi-Hung Liu, Shiuh-Tzung Liu

引用次数: 0

Abstract

Highly substituted naphthalene derivatives were prepared via palladium-catalyzed reaction of 5-(2-bromophenyl)pent-3-en-1-ynes with arylboronic acids. Typically, reaction of 3-bromo-4-(3-(4-chlorophenyl)-5-phenyl-1-(p-tolyl)pent-2-en-4-yn-1-yl)-N-methylaniline (1a) with PhB(OH)₂ in the presence of Pd(PPh₃)₄ as the catalyst under basic conditions provided 8-benzhydryl-7-(4-chlorophenyl)-N-methyl-5-(p-tolyl)naphthalen-2-amine (2a) quantitatively. Overall, 19 new naphthalene compounds were obtained by this methodology and their structures were characterized by spectroscopic methods. In addition, crystal structure of 2j was determined to confirm the structural details. Reaction pathway leading to the desired product is also discussed.

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在 Suzukii-Miyaura 偶联条件下，通过 Pd 催化 5-(2-溴苯基)戊-3-烯-1-炔环化制备萘

通过钯催化 5-(2-溴苯基)戊-3-烯-1-炔与芳基硼酸的反应，制备了高取代萘衍生物。通常情况下，3-溴-4-(3-(4-氯苯基)-5-苯基-1-(对甲苯基)戊-2-烯-4-炔-1-基)-N-甲基苯胺(1a)与 PhB(OH)2，在 Pd(PPh3)4 作为催化剂存在下，在碱性条件下反应，可定量提供 8-二苯甲基-7-(4-氯苯基)-N-甲基-5-(对甲苯基)萘-2-胺(2a)。通过该方法共获得了 19 个新的萘化合物，并通过光谱方法对其结构进行了表征。此外，还测定了 2j 的晶体结构，以确认其结构细节。此外，还讨论了得到所需产物的反应途径。

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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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

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