Merging π-Acid and Pd Catalysis: Dearomatizing Spirocyclization/Cross-Coupling Cascade Reactions of Alkyne-Tethered Aromatics

被引：58
|
作者：
Ho, Hon Eong [1 ]
Stephens, Thomas C. [1 ]
Payne, Thomas J. [1 ]
O'Brien, Peter [1 ]
Taylor, Richard J. K. [1 ]
Unsworth, William P. [1 ]
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
ACS CATALYSIS | 2019年 / 9卷 / 01期
基金：
英国工程与自然科学研究理事会;
关键词：
spirocycles; dearomatization; cross-coupling; palladium; catalysis; VISIBLE-LIGHT PHOTOREDOX; N-ARYLPROPIOLAMIDES; ASYMMETRIC DEAROMATIZATION; ARYLATIVE CYCLIZATION; OXIDATIVE ANNULATION; ARYLDIAZONIUM SALTS; ACTIVATED ALKYNES; MOLECULAR-OXYGEN; METAL CATALYSIS; C-N;
D O I：
10.1021/acscatal.8b03861
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A one-pot protocol for the dearomatizing spirocyclization/cross-coupling of alkyne-tethered indoles/pyrroles is described. Mechanistic studies support a process by which palladium complexes generated in situ act as both pi acid and cross-coupling catalysts. Overall, this facilitates an efficient cascade process that enables the simultaneous preparation of synthetically challenging quaternary spirocyclic carbons and tetrasubstituted alkenes in a single operation.
引用
收藏
页码：504 / 510
页数：13
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