Xiaodan Zhao

Name: 赵晓丹; Zhao, XiaoDan

Organization: Sun Yat-Sen University , China

Department: Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry

Title: Professor(PhD)

Chemicals
References

Combination of Lewis Basic Selenium Catalysis and Redox Selenium Chemistry: Synthesis of Trifluoromethylthiolated Tertiary Alcohols with Alkenes

Co-reporter:Zechen Zhu, Jie Luo, and Xiaodan Zhao

Organic Letters September 15, 2017 Volume 19(Issue 18) pp:

Publication Date(Web):September 6, 2017

DOI:10.1021/acs.orglett.7b02406

A new and efficient method for diaryl selenide catalyzed vicinal CF3S hydroxylation of 1,1-multisubstitued alkenes has been developed. Various trifluoromethylthiolated tertiary alcohols could be readily synthesized under mild conditions. This method is also effective for the intramolecular cyclization of alkenes tethered by carboxylic acid, hydroxy, sulfamide, or ester groups and is associated with the introduction of a CF3S group. Mechanistic studies have revealed that the pathway involves a redox cycle between Se(II) and Se(IV) and Lewis basic selenium catalysis.

Chiral Selenide-Catalyzed Enantioselective Construction of Saturated Trifluoromethylthiolated Azaheterocycles

Co-reporter:Jie Luo, Yannan Liu, and Xiaodan Zhao

Organic Letters July 7, 2017 Volume 19(Issue 13) pp:

Publication Date(Web):June 20, 2017

DOI:10.1021/acs.orglett.7b01392

An indane-based, bifunctional, chiral selenide catalyst has been developed. The new catalyst is efficient for the enantioselective synthesis of saturated azaheterocycles possessing a trifluoromethylthio group. The desired products were obtained in good yields with high diastereo- and enantioselectivities.

Organoselenium-Catalyzed Synthesis of Oxygen- and Nitrogen-Containing Heterocycles

Co-reporter:Ruizhi Guo, Jiachen Huang, Haiyan Huang, and Xiaodan Zhao

Organic Letters 2016 Volume 18(Issue 3) pp:504-507

Publication Date(Web):January 22, 2016

DOI:10.1021/acs.orglett.5b03543

A new and efficient approach for the synthesis of oxygen and nitrogen heterocycles by organoselenium catalysis has been developed. The exo-cyclization proceeded smoothly under mild conditions with good functional group tolerance and excellent regioselectivity. Mechanistic studies revealed that 1-fluoropyridinium triflate is key for oxidative cyclization.

Innenrcktitelbild: Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide (Angew. Chem. 19/2016)

Co-reporter:Xiang Liu;Rui An;Dr. Xuelin Zhang;Jie Luo ;Dr. Xiaodan Zhao

Angewandte Chemie 2016 Volume 128( Issue 19) pp:

Publication Date(Web):

DOI:10.1002/ange.201603087

Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide

Co-reporter:Xiang Liu;Rui An;Dr. Xuelin Zhang;Jie Luo ;Dr. Xiaodan Zhao

Angewandte Chemie 2016 Volume 128( Issue 19) pp:5940-5944

Publication Date(Web):

DOI:10.1002/ange.201601713

Abstract

Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane-based bifunctional chiral sulfide catalyst and a shelf-stable electrophilic SCF₃ reagent. The desired products were formed with diastereoselectivities of >99:1 and good to excellent enantioselectivities. The transformation represents the first enantioselective trifluoromethylthiolation of alkenes and the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center.

Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide

Co-reporter:Xiang Liu;Rui An;Dr. Xuelin Zhang;Jie Luo ;Dr. Xiaodan Zhao

Angewandte Chemie International Edition 2016 Volume 55( Issue 19) pp:5846-5850

Publication Date(Web):

DOI:10.1002/anie.201601713

Abstract

Inside Back Cover: Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide (Angew. Chem. Int. Ed. 19/2016)

Co-reporter:Xiang Liu;Rui An;Dr. Xuelin Zhang;Jie Luo ;Dr. Xiaodan Zhao

Angewandte Chemie International Edition 2016 Volume 55( Issue 19) pp:

Publication Date(Web):

DOI:10.1002/anie.201603087

Diaryl Selenide Catalyzed Vicinal Trifluoromethylthioamination of Alkenes

Co-reporter:Jie Luo, Zechen Zhu, Yannan Liu, and Xiaodan Zhao

Organic Letters 2015 Volume 17(Issue 14) pp:3620-3623

Publication Date(Web):July 9, 2015

DOI:10.1021/acs.orglett.5b01727

An efficient approach to vicinal trifluoromethylthioamination of alkenes with a broad substrate scope catalyzed by electron-rich diaryl selenide has been developed. This intermolecular amination strategy was successfully applied to SCF3-esterification of alkenes using weak acids as nucleophiles.

Organoselenium-Catalyzed, Hydroxy-Controlled Regio- and Stereoselective Amination of Terminal Alkenes: Efficient Synthesis of 3-Amino Allylic Alcohols

Co-reporter:Zhimin Deng, Jialiang Wei, Lihao Liao, Haiyan Huang, and Xiaodan Zhao

Organic Letters 2015 Volume 17(Issue 8) pp:1834-1837

Publication Date(Web):April 7, 2015

DOI:10.1021/acs.orglett.5b00213

An efficient route to prepare 3-amino allylic alcohols in excellent regio- and stereoselectivity in the presence of bases by orangoselenium catalysis has been developed. In the absence of bases α,β-unsaturated aldehydes were formed in up to 97% yield. Control experiments reveal that the hydroxy group is crucial for the direct amination.

Organoselenium-catalyzed synthesis of indoles through intramolecular C–H amination

Co-reporter:Xuelin Zhang, Ruizhi Guo and Xiaodan Zhao

Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 10) pp:NaN1337-1337

Publication Date(Web):2015/07/29

DOI:10.1039/C5QO00179J

A new and efficient route for organoselenium-catalyzed synthesis of indoles via intramolecular C–H amination has been developed. The reaction conditions were mild and the desired products were formed in up to 99% yield. When the method was applied in the reaction of a trisubstituted alkene, the corresponding indole was obtained in 99% yield via 1,2-phenyl migration.