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Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters.
Org Lett 2019; 21(10):3774-3779OL

Abstract

A convenient visible-light photoredox catalysis has been developed for the synthesis of thioesters from two readily available starting materials: acid chlorides and sodium sulfinates. The facile generation of acyl radical species under the visible light photoredox conditions allows the formation of thiyl radical species from sodium sulfinates via multiple single electron transfer reactions, where the final acyl radical-thiyl radical coupling has been accomplished. The direct radical-radical coupling strategy offers a mild and controlled photochemical approach to important synthetic building blocks such as thioesters.

Authors+Show Affiliations

Center for Metareceptome Research, College of Pharmacy , Chung-Ang University , 84 Heukseok-ro , Dongjak, Seoul 06974 , Republic of Korea.Center for Metareceptome Research, College of Pharmacy , Chung-Ang University , 84 Heukseok-ro , Dongjak, Seoul 06974 , Republic of Korea.Center for Metareceptome Research, College of Pharmacy , Chung-Ang University , 84 Heukseok-ro , Dongjak, Seoul 06974 , Republic of Korea.Center for Metareceptome Research, College of Pharmacy , Chung-Ang University , 84 Heukseok-ro , Dongjak, Seoul 06974 , Republic of Korea.

Pub Type(s)

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

Language

eng

PubMed ID

31062986

Citation

Bogonda, Ganganna, et al. "Visible-Light-Promoted Thiyl Radical Generation From Sodium Sulfinates: a Radical-Radical Coupling to Thioesters." Organic Letters, vol. 21, no. 10, 2019, pp. 3774-3779.
Bogonda G, Patil DV, Kim HY, et al. Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters. Org Lett. 2019;21(10):3774-3779.
Bogonda, G., Patil, D. V., Kim, H. Y., & Oh, K. (2019). Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters. Organic Letters, 21(10), pp. 3774-3779. doi:10.1021/acs.orglett.9b01218.
Bogonda G, et al. Visible-Light-Promoted Thiyl Radical Generation From Sodium Sulfinates: a Radical-Radical Coupling to Thioesters. Org Lett. 2019 05 17;21(10):3774-3779. PubMed PMID: 31062986.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters. AU - Bogonda,Ganganna, AU - Patil,Dilip V, AU - Kim,Hun Young, AU - Oh,Kyungsoo, Y1 - 2019/05/07/ PY - 2019/5/8/pubmed PY - 2019/5/8/medline PY - 2019/5/8/entrez SP - 3774 EP - 3779 JF - Organic letters JO - Org. Lett. VL - 21 IS - 10 N2 - A convenient visible-light photoredox catalysis has been developed for the synthesis of thioesters from two readily available starting materials: acid chlorides and sodium sulfinates. The facile generation of acyl radical species under the visible light photoredox conditions allows the formation of thiyl radical species from sodium sulfinates via multiple single electron transfer reactions, where the final acyl radical-thiyl radical coupling has been accomplished. The direct radical-radical coupling strategy offers a mild and controlled photochemical approach to important synthetic building blocks such as thioesters. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/31062986/Visible_Light_Promoted_Thiyl_Radical_Generation_from_Sodium_Sulfinates:_A_Radical_Radical_Coupling_to_Thioesters_ L2 - https://dx.doi.org/10.1021/acs.orglett.9b01218 DB - PRIME DP - Unbound Medicine ER -