摘要/Abstract
开发了一种铂催化氧杂二环烯烃与芳基磺酰肼的顺式-立体控制开环反应.该方法显示出高效性和良好的官能团耐受性，在温和条件下能以高达89%的产率得到顺式-2-芳基-1，2-二氢萘-1-醇（3）或脱水产物2-芳基萘（4）.此外，通过X射线单晶衍射分析确认了产物（1S*，2R*）-6，7-二溴-2-（4-甲基苯基）-1，2-二氢萘-1-醇（3db）的顺式-1，2-构型.根据实验结果，提出了一种合理的开环反应机理.值得注意的是，在开环反应中，芳基磺酰肼通过释放N2和SO2形成碳负离子作为亲核试剂.
关键词: 铂催化剂, 开环, 氧杂二环烯烃, 芳基磺酰肼, 亲核试剂
A platinum-catalyzed syn-stereocontrolled ring-opening reaction of oxabicyclic alkenes with arylsulfonyl hydrazides was developed. This protocol exhibited high efficiency and good functional group tolerance, affording cis-2-aryl-1,2-dihydronaphthalen-1-ols (3) or 2-aryl-naphthalenes (4) as dehydrated products in good to excellent yields under mild conditions (up to 89%). In addition, the cis-1,2-configuration of product (1S*,2R*)-6,7-dibromo-2-(p-tolyl)-1,2-dihydronaphthalen-1-ol (3db) was confirmed by X-ray single crystal diffraction analysis. Based on the results, a plausible mechanism for the ring-opening reaction was proposed. Remarkably, arylsulfonyl hydrazides were used as carboanion nucleophiles in the ring-opening reaction via releasing N2 and SO2 in situ.
Key words: platinum catalyst, ring-opening, oxabicyclic alkenes, arylsulfonyl hydrazides, nucleophiles
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