Cobalt-Catalyzed Cross-Coupling of Glycosyl Sulfones with Zinc reagents toward the Stereoselective Synthesis of C(sp/sp<sup>2</sup>)-Glycosides

A cobalt-catalyzed desulfonylative cross-coupling of glycosyl sulfones with organozinc reagents toward the stereoselective synthesis of C-glycosides is reported. The new C-glycoside synthesis proceeds under mild reaction conditions and exhibits tolerance to a range of functional groups. Diverse alkynylated, arylated, and alkenylated products are formed with high efficiency and excellent diastereoselectivity. Mechanistic studies indicate a radical pathway.

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Publication Details

Journal
Organic Letters
Published
2025-04-18
DOI
https://doi.org/10.1021/acs.orglett.5c01091
Citations
2
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
1.87

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article

Cobalt-Catalyzed Cross-Coupling of Glycosyl Sulfones with Zinc reagents toward the Stereoselective Synthesis of C(sp/sp2)-Glycosides

Xinyue Hu, Xu‐Ge Liu, Xiaoli Wang, Miaomiao Wen et al.
2 citations
Organic Letters
Carbohydrate Chemistry and Synthesis
1.87
article

Cobalt-Catalyzed Cross-Coupling of Glycosyl Sulfones with Zinc reagents toward the Stereoselective Synthesis of C(sp/sp2)-Glycosides

Xinyue Hu, Xu‐Ge Liu, Xiaoli Wang, Miaomiao Wen, Pengfei Wang, Cong-Zhen Zhang, Yu-Jun Ruan
article en
2 citations

Abstract

A cobalt-catalyzed desulfonylative cross-coupling of glycosyl sulfones with organozinc reagents toward the stereoselective synthesis of C-glycosides is reported. The new C-glycoside synthesis proceeds under mild reaction conditions and exhibits tolerance to a range of functional groups. Diverse alkynylated, arylated, and alkenylated products are formed with high efficiency and excellent diastereoselectivity. Mechanistic studies indicate a radical pathway.

Organic LettersVol. 27(17)
Henan University (CN)
National Natural Science Foundation of China, Henan University, Natural Science Foundation of Henan Province
Clean water and sanitation
Openalex Percentile: Top 16%
Carbohydrate Chemistry and Synthesis
1.87
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