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铑(III)催化的芳基酮 O-酰氧基肟衍生物和内部炔烃合成异喹啉。

Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes.

机构信息

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

出版信息

Org Lett. 2010 Dec 17;12(24):5688-91. doi: 10.1021/ol102504b. Epub 2010 Nov 17.

Abstract

A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using Cp*RhCl(2)-NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C-H vinylation via ortho-rhodation and C-N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N-O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

摘要

已开发出一种使用 Cp*RhCl(2)-NaOAc 作为潜在催化剂体系,由芳基酮 O-酰肟衍生物和内炔合成异喹啉的方法。这种转化是通过氧化铱中间体的邻位铱化和 C-N 键形成的氧化还原中性 C-H 乙烯基化序列进行的,其中肟衍生物的 N-O 键可以作为内部氧化剂来维持催化循环。

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