Manganese(I)-Catalyzed C-H (2-Indolyl)methylation: Expedient Access to Diheteroarylmethanes

被引:83
作者
Lu, Qingquan [1 ]
Cembellin, Sara [1 ]
Gressies, Steffen [1 ]
Singha, Santanu [1 ]
Daniliuc, Constantin G. [1 ]
Glorius, Frank [1 ]
机构
[1] Westfal Wilhelms Univ Munster, Organ Chem Inst, Corrensstr 40, D-48149 Munster, Germany
关键词
C-H activation; diheteroarylmethane derivatives; ethynyl benzoxazinanone; (2-indolyl)methylation; manganese; MANGANESE-CATALYZED SYNTHESIS; BOND FORMATION; ROBUSTNESS SCREEN; CASCADE REACTION; 4+2 ANNULATION; ACTIVATION; FUNCTIONALIZATION; HETEROARYLATION; ESTERS; IMINES;
D O I
10.1002/anie.201710060
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unprecedented Mn-I-catalyzed (2-indolyl)methylation of heteroarenes is reported. This method makes use of an aromatizing cascade strategy to install a (2-indolyl)methyl group into target molecules, thereby leading to the expedient synthesis of previously challenging and important unsymmetrical diheteroarylmethanes, in particular bis(2-indolyl)methanes. The proposed cascade process comprises the reorganization of multiple bonds with controlled regioselectivity and high atom economy and can be performed on a gram-scale. Furthermore, a metal-free C-H propargylation is observed. The diverse application of this method is also demonstrated.
引用
收藏
页码:1399 / 1403
页数:5
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