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Iron-Promoted Difunctionalization of Alkenes by Phenylselenylation/1,2-Aryl Migration
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-22 00:00:00 , DOI: 10.1021/acs.orglett.7b02751 Ping Wu 1, 2 , Kaikai Wu 1 , Liandi Wang 1 , Zhengkun Yu 1, 3
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-22 00:00:00 , DOI: 10.1021/acs.orglett.7b02751 Ping Wu 1, 2 , Kaikai Wu 1 , Liandi Wang 1 , Zhengkun Yu 1, 3
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Iron-promoted difunctionalization of α,α-diaryl and α-aryl-α-alkyl allylic alcohols has been efficiently achieved by means of N-(phenylseleno)phthalimide (N-PSP) under mild conditions. An in situ generated phenylselenium cation (PhSe+) was added to the olefinic C═C bond to initiate the regioselective phenylselenylation with concomitant 1,2-aryl migration, following a migration preference contrary to the well-known radical pathway. Hydrazonation of the resultant alkene difunctionalization products, that is, α-aryl-β-phenylselenyl ketones, and subsequent copper-catalyzed dehydroselenylation efficiently afforded functionalized 2-pyrazoline derivatives.
中文翻译：
铁通过苯基硒基化/ 1,2-芳基迁移促进烯烃的双官能化
铁，α，α-二芳基和α-芳基-α-烷基烯丙基醇的双官能化已在温和的条件下通过N-（苯基硒代）邻苯二甲酰亚胺（N-PSP）有效地实现了。将原位生成的苯基硒阳离子（PhSe +）添加到烯烃的C═C键上，以一种与众所周知的自由基途径相反的迁移偏好，伴随着1,2-芳基迁移，引发区域选择性的苯基硒基化反应。所得到的烯烃双官能化产物，即α-芳基-β-苯基硒烯酮的氢解，以及随后的铜催化的脱氢硒烯化有效地提供了官能化的2-吡唑啉衍生物。
更新日期：2017-09-22
中文翻译：
铁通过苯基硒基化/ 1,2-芳基迁移促进烯烃的双官能化
铁，α，α-二芳基和α-芳基-α-烷基烯丙基醇的双官能化已在温和的条件下通过N-（苯基硒代）邻苯二甲酰亚胺（N-PSP）有效地实现了。将原位生成的苯基硒阳离子（PhSe +）添加到烯烃的C═C键上，以一种与众所周知的自由基途径相反的迁移偏好，伴随着1,2-芳基迁移，引发区域选择性的苯基硒基化反应。所得到的烯烃双官能化产物，即α-芳基-β-苯基硒烯酮的氢解，以及随后的铜催化的脱氢硒烯化有效地提供了官能化的2-吡唑啉衍生物。
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