Facile synthesis of diverse hetero polyaromatic hydrocarbons (PAHs) via the styryl Diels–Alder reaction of conjugated diynes
Facile synthesis of diverse hetero polyaromatic hydrocarbons (PAHs) via the styryl Diels–Alder reaction of conjugated diynes
复制标题
通过共轭二炔的苯乙烯基狄尔斯-阿尔德反应轻松合成多种杂多芳烃 (PAH)
DOI：
10.1039/d2qo00644h
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发表时间：
2022
影响因子：
5.4
通讯作者：
Shi, Xiaodong
中科院分区：
文献类型：
--
作者：
Wei, Jingwen;Liu, Mengjia;Ye, Xiaohan;Zhang, Shuyao;Sun, Elaine;Shan, Chuan;Wojtas, Lukasz;Shi, Xiaodong
本文报道了苯乙烯基与共轭二炔的脱氢Diels-桤木反应。虽然典型的炔-苯乙烯缩合需要升高的温度（>160 °C），但共辄二炔的应用允许在较温和的条件（80 °C）下有效转化。热稳定的三唑-金（TA-Au）催化剂进一步提高了反应产率（高达95%），在一个单一的步骤中与分子氧作为氧化剂产生所需的炔基萘。连续的炔活化导致各种多环芳烃（PAHs）在优异的产率，突出了这种新策略的效率，为制备具有良好的官能团耐受性和结构多样性的多环芳烃。
The styryl dehydro-Diels–Alder reaction with a conjugated diyne is reported. While typical alkyne–styrene condensation requires elevated temperatures (>160 °C), the application of a conjugated diyne allowed for effective transformation under milder conditions (80 °C). The thermally stable triazole–gold (TA–Au) catalyst further improved the reaction yields (up to 95%), producing the desired alkynyl–naphthalene in a single step with molecular oxygen as the oxidant. Sequential alkyne activation resulted in various polyaromatic hydrocarbons (PAHs) in excellent yields, highlighting the efficiency of this new strategy for the preparation of PAHs with good functional group tolerance and structural diversity.