Copper-Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction

被引：12

作者：

Rodriguez, Anabel M. ^{[1
,2
]}

Molina, Francisco ^{[1
,2
]}

Diaz-Requejo, M. Mar ^{[1
,2
]}

Perez, Pedro J. ^{[1
,2
]}

机构：

[1] Univ Huelva, Unidad Asociada CSIC, Lab Catalisis Homogenea, CIQSO,Ctr Invest Quim Sosten, Campus El Carmen S-N, Huelva 21007, Spain

[2] Univ Huelva, Dept Quim, Campus El Carmen S-N, Huelva 21007, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 10期

关键词：

Pyrrole functionalization; copper catalysis; carbene transfer; diazo compounds; C-H functionalization; selectivity; STEREOSELECTIVE-SYNTHESIS; INDOLES; HETEROCYCLES; ACTIVATION; ALKANES; BONDS;

D O I：

10.1002/adsc.201901629

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

1H-Pyrroles can be directly functionalized by means of the incorporation of carbene groups from diazo compounds, in a process catalyzed by Tp(x)Cu complexes (Tp(x)=hydrotrispyrazolylborate ligand). The reactions take place with a complete selectivity toward the formal insertion of the carbene into the C-alpha-H bond, leading to alkylated pyrroles, with no modification of the C-beta-H, N-H or C=C bonds of the pyrrole unit. Alkyl substituents at C-ring as well as alkyl, aryl, allyl or alkyne substitution at N atom are tolerated, the strategy affording 20 new pyrrole derivatives. The observance of partial deuteration at the methylene group when the reaction is carried out with added D2O serves to discard the direct insertion of the carbene group into the C-sp2-H bond, the alternative electrophilic attack to the pyrrole ring being feasible.

引用

页码：1998 / 2004

页数：7

共 30 条

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