Synthesis of Dibenzosultams by "Transition-Metal-Free" Photoinduced Intramolecular Arylation of N-Aryl-2-halobenzenesulfonamides

被引：30

作者：

Guerra, Walter D. ^{[1
]}

Rossi, Roberto A. ^{[1
]}

Pierini, Adriana B. ^{[1
]}

Barolo, Silvia M. ^{[1
]}

机构：

[1] Univ Nacl Cordoba, Fac Ciencias Quim, Dept Quim Organ, INFIQC, Ciudad Univ, RA-5000 Cordoba, Argentina

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 12期

关键词：

CATALYZED N-ARYLATION; AB-INITIO; DENSITY FUNCTIONALS; ARYL BROMIDES; SULFONAMIDES; CONTINUUM; IODIDES; ENERGY;

D O I：

10.1021/acs.joc.6b00330

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and general synthetic route to prepare dibenzosultams is here reported. This approach involves the synthesis of N-aryl-2-halobenzenesulfonamides (3), followed by intramolecular C-C photoinduced arylation under soft conditions without the use of "Transition Metal". The photostimulated reactions exhibit very good tolerance to different substituent groups with good to excellent isolated yields (42-98%) of products. Moreover, it is shown that LED (lambda = 395 nm) is an efficient light energy source to initiate efficiently the reactions. Theoretical inspection of the: mechanism was made to probe the involvement of the radical-anion S(RN)1 process.

引用

页码：4965 / 4973

页数：9

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