Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy

Ya-Nan Ding; Yan-Chong Huang; Wei-Yu Shi; Nian Zheng; Cui-Tian Wang; Xi Chen; Yang An; Zhe Zhang; Yong-Min Liang

doi:10.1021/acs.orglett.1c01723

Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy

Org Lett. 2021 Aug 6;23(15):5641-5646. doi: 10.1021/acs.orglett.1c01723. Epub 2021 Jul 12.

Authors

Ya-Nan Ding¹, Yan-Chong Huang¹, Wei-Yu Shi¹, Nian Zheng¹, Cui-Tian Wang¹, Xi Chen¹, Yang An¹, Zhe Zhang¹, Yong-Min Liang¹

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.

PMID: 34251824
DOI: 10.1021/acs.orglett.1c01723

Abstract

We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%, 53 examples). This method enables the straightforward formation of the C(sp²)-S/Se bond of (hetero)aryl thio/selenoglycosides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Iodides / chemistry*
Molecular Structure
Organoselenium Compounds / chemical synthesis*
Organoselenium Compounds / chemistry
Palladium / chemistry

Substances

Iodides
Organoselenium Compounds
Palladium