Synthesis of Indoles through Palladium-Catalyzed Three-Component Reaction of Aryl Iodides, Alkynes, and Diaziridinone
The three-component reaction of aryl iodides, alkynes, and diaziridinone is described. The reaction provides an innovative synthetic approach for indoles. The approach features high efficiency, broad substrate scope, and excellent regioselectivity. C,C-Palladacycles should act as the intermediates. The C,C-palladacycles are obtained from simple aryl halides and alkynes and then reacted with diaziridinone to afford indoles.
期刊:
Organic Letters
2018
作者:
Yanghui Zhang,Xiaoming Ji,Ding Ma,Zhuo Wu,Bo Zhou
DOI:10.1021/acs.orglett.8b02750
Synthesis of 9,9-Disubstituted Fluorenes from 2-Iodobiphenyls and α-Diazoesters under Palladium Catalysis
9,9-Disubstituted fluorenes are widely employed in materials science. We have developed a straightforward approach for the synthesis of 9,9-disubstituted fluorenes from 2-iodobiphenyls and α-diazoesters. The reaction proceeds via a tandem palladium-catalyzed C(sp2)–H activation/carbenoid insertion sequence.
期刊:
The Journal of Organic Chemistry
2018
作者:
Yanghui Zhang,Xiaoming Ji,Zhuo Wu,Guangfa Shi,Ding Ma
DOI:10.1021/acs.joc.7b02885
The Synthesis of Benzofulvenes through Palladium-Catalyzed Sequential Three-Component Reactions
An approach for the synthesis of benzofulvenes has been developed through palladium‐catalyzed sequential three‐component reactions. The reactions likely involve C,C‐palladacycles as the key intermediates. The palladacycles are generated through cascade reactions of aryl halides and alkynes, and then reacted with CH2Br2 to form benzofulvenes as the final products.
期刊:
Advanced Synthesis & Catalysis
2018
作者:
Yanghui Zhang,Xueliang Sun,Weixin Qi,Zhuo Wu,Bo Zhou
DOI:10.1002/adsc.201801141
An approach to spirooxindoles via palladium-catalyzed remote C–H activation and dual alkylation with CH2Br2
A facile and efficient approach for the synthesis of spirooxindoles has been developed via the coupling of spirocyclic C,C-palladacycles with CH2Br2. The key spirocyclic palladacycles are generated catalytically via remote C–H activation. A range of spirooxindoles can be synthesized in good to excellent yields from readily available starting material.
期刊:
Chemical Communications
2017
作者:
Yanghui Zhang,Bo Zhou,Xiaoming Ji,Zhuo Wu,Changdong Shao
DOI:10.1039/c7cc06196j
Palladium-Catalyzed C−H Silylation through Palladacycles Generated from Aryl Halides
A highly efficient palladium‐catalyzed disilylation reaction of aryl halides through C−H activation has been developed for the first time. The reaction has broad substrate scope. A variety of aryl halides can be disilylated by three types of C−H activation, including C(sp2)−H, C(sp3)−H, and remote C−H activation. In particular, the reactions are also unusually efficient. The yields are essentially quantitative in many cases, even in the presence of less than 1 mol % catalyst and 1 equivalent of the silylating reagent under relatively mild conditions. The disilylated biphenyls can be converted into disiloxane‐bridged biphenyls.
期刊:
Angewandte Chemie International Edition
2017
作者:
Yanghui Zhang,Zhuo Wu,Bo Zhou,Xiaoming Ji,Ailan Lu
DOI:10.1002/anie.201800330
Synthesis of Carbazoles from 2-Iodobiphenyls by Palladium-Catalyzed C−H Activation and Amination with Diaziridinone
A facile and efficient approach has been developed for the synthesis of carbazoles from 2‐iodobiphenyls and diaziridinone under palladium catalysis. A wide range of carbazoles were synthesized in good to excellent yields, and indole derivatives were obtained by using styrenes as the substrate. The palladacycles obtained from 2‐iodobiphenyls acted as the key intermediate, and the reaction should proceed via a tandem Pd‐catalyzed C−H activation/dual C−N bond formation sequence.
期刊:
Advanced Synthesis & Catalysis
2017
作者:
Yanghui Zhang,Xiaoming Ji,Zhuo Wu,Bo Zhou,Changdong Shao
DOI:10.1002/adsc.201701039
Palladium-Catalyzed Alkylation with Alkyl Halides by C(sp3
)−H Activation
Utilizing halogens as traceless directing goups represents an attractive strategy for C−H functionalization. A two C−H alkylation system, initiated by the oxidative addition of organohalides to Pd0, has been developed. The first reaction involves an intermolecular alkylation of palladacycles to form C(sp3)−C(sp2) bonds followed by C(sp2)−H activation/cyclization to deliver alkylated benzocyclobutenes as the final products. In the second reaction, two C−C bonds are formed by the reaction of palladacycles with CH2Br2, and provides a facile and efficient method for the synthesis of indanes. The alkylated benzocyclobutene products can be transformed into tricyclic hyrocarbons, and the indane derivatives are essential structural motifs in bioactive and odorant molecules.
期刊:
Angewandte Chemie International Edition
2017
作者:
Yanghui Zhang,Xiaoling Wang,Xiaotian Ma,Xiaoming Ji,Bo Zhou,Ding Ma,Zhuo Wu
DOI:10.1002/anie.201706418
