Rhodium-Catalyzed Synthesis of 4-Bromo-1,2-dihydroisoquinolines: Access to Bromonium Ylides by the Intramolecular Reaction of a Benzyl Bromide and an -Imino Carbene

Rhodium-Catalyzed Synthesis of 4-Bromo-1,2-dihydroisoquinolines: Access to Bromonium Ylides by the Intramolecular Reaction of a Benzyl Bromide and an -Imino Carbene
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铑催化合成 4-溴-1,2-二氢异喹啉:通过苄基溴和 α-亚氨基卡宾的分子内反应获得溴叶立德

DOI:
10.1002/anie.201512015
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发表时间:
2016-03-24
影响因子:
16.6
通讯作者:
Li, Chuan-Ying
Li, Chuan-Ying
中科院分区:
化学1区
文献类型:
--
作者:
He, Jun;Shi, Yinping;Li, Chuan-Ying

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以4-(2-(溴甲基)苯基)-1-磺酰基-1,2,3-三唑为原料合成了高度官能化的4-溴-1,2-二氢异喹啉。一个溴叶立德提出的关键中间体,它可以形成的分子内亲核攻击的苄基溴上的-亚氨基铑卡宾在铑催化剂的存在下形成。
Highly functionalized 4-bromo-1,2-dihydroisoquinolines were synthesized from readily available 4-(2-(bromomethyl)phenyl)-1-sulfonyl-1,2,3-triazoles. A bromonium ylide is proposed as the key intermediate, which can be formed by the intramolecular nucleophilic attack of the benzyl bromide on the -imino rhodium carbene formed in the presence of the rhodium catalyst.