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Catalyst-Free Double CH-Functionalization of Quinolines with Phosphine Oxides via Two SNHAr Reaction Sequences
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-25 , DOI: 10.1021/acs.joc.0c00084 Boris A. Trofimov 1 , Pavel A. Volkov 1 , Anton A. Telezhkin 1 , Kseniya O. Khrapova 1 , Nina I. Ivanova 1 , Alexander I. Albanov 1 , Nina K. Gusarova 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-25 , DOI: 10.1021/acs.joc.0c00084 Boris A. Trofimov 1 , Pavel A. Volkov 1 , Anton A. Telezhkin 1 , Kseniya O. Khrapova 1 , Nina I. Ivanova 1 , Alexander I. Albanov 1 , Nina K. Gusarova 1
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Quinolines undergo catalyst-free double CH-functionalization upon treatment with secondary phosphine oxides (70–75 °C, 20–48 h) followed by oxidation of the intermediate 2,4-bisphosphoryltetrahydroquinolines with chloranil. The yields of the target 2,4-bisphosphorylated quinolines are up to 77%. Thus, a double-SNHAr reaction sequence in the same molecule of quinoline has been realized. In the case of 2,4-bisphenylphosphoryltetrahydroquinolines, the aromatization occurs with elimination of one molecule of diphenylphosphine oxide to afford the products of monofunctionalization, 4-diphenylphosphorylquinolines, in 40–45% yields.
中文翻译：
通过两个S N H Ar反应序列用氧化膦将喹啉进行无催化剂的双CH功能化
喹啉经过仲膦氧化物（70-75°C，20-48 h）处理后，经过无催化剂的双CH官能化，然后用氯苯腈氧化中间体2,4-双磷酰基四氢喹啉。目标2,4-双磷酸化喹啉的产率高达77％。因此，已经实现了在相同的喹啉分子中的双S N H Ar反应序列。在2,4-双苯基磷酰基四氢喹啉的情况下，通过消除一分子的二苯基氧化膦来进行芳构化，从而以40-45％的产率提供单官能化的产物4-二苯基磷酰基喹啉。
更新日期：2020-03-26
中文翻译：
通过两个S N H Ar反应序列用氧化膦将喹啉进行无催化剂的双CH功能化
喹啉经过仲膦氧化物（70-75°C，20-48 h）处理后，经过无催化剂的双CH官能化，然后用氯苯腈氧化中间体2,4-双磷酰基四氢喹啉。目标2,4-双磷酸化喹啉的产率高达77％。因此，已经实现了在相同的喹啉分子中的双S N H Ar反应序列。在2,4-双苯基磷酰基四氢喹啉的情况下，通过消除一分子的二苯基氧化膦来进行芳构化，从而以40-45％的产率提供单官能化的产物4-二苯基磷酰基喹啉。
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