4-Diazoisochroman-3-imines: A Class of Metal Carbene Precursors for the Synthesis of Isochromene Derivatives
4-Diazoisochroman-3-imines: A Class of Metal Carbene Precursors for the Synthesis of Isochromene Derivatives
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4-重氮异色满-3-亚胺：一类用于合成异色烯衍生物的金属卡宾前体
DOI：
10.1021/acs.joc.7b01860
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发表时间：
2017
期刊：
影响因子：
--
通讯作者：
Yanguang Wang
中科院分区：
文献类型：
--
作者：
Anni Ren;Bo Lang;Jialun Lin;Ping Lu;Yanguang Wang
研究了 4-重氮异色满-3-亚胺作为一类新型金属卡宾前体的合成应用。在Rh(II)配合物的催化下，这类α-重氮亚胺酸酯与烯烃和共轭二烯通过正式的[2 + 1]（即环丙烷化）或[4 + 3]环加成反应，分别生成螺[环丙烷-1,4'-异色满]-3'-亚胺和四氢异色烯[3,4-b]氮杂卓。当使用Rh(II)/AgOTf作为助催化剂时，4-重氮异苯并二氢吡喃-3-亚胺与末端炔发生正式[3+2]环加成，从而合成2-芳基-3,5-二氢异苯并[3,4-b]吡咯。
4-Diazoisochroman-3-imines were investigated for their synthetic applications as a new class of metal carbene precursors. Under the catalysis from a Rh(II) complex, this class of α-diazo imidates reacted with alkenes and conjugated dienes through a formal [2 + 1] (i.e., cyclopropanation) or [4 + 3] cycloaddition to furnish spiro[cyclopropane-1,4′-isochroman]-3′-imines and tetrahydroisochromeno[3,4-b] azepines, respectively. When Rh(II)/AgOTf was used as cocatalyst, the formal [3 + 2] cycloaddition of 4-diazoisochroman-3-imines with terminal alkynes took place, leading to the synthesis of 2-aryl-3,5-dihydroisochromeno[3,4-b]pyrroles.