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Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents.
Org Lett 2018; 20(19):6239-6243OL

Abstract

A new neutral silicon-based traceless activation group (TAG) for visible-light photoredox-catalyzed hydroalkoxymethylation of alkenes is presented. This reaction involves in-situ-generated alkoxymethyl radical via single electron oxidation (SET) of α-TMS-substituted ethers, followed by subsequent conjugate addition to activated alkenes. Various functional groups were tolerated both under mild metal and metal-free conditions to provide good to excellent yields. Furthermore, the addition products were transformed to valuable synthetic building blocks, such as carboxylic acids, γ-butyrolactones, and complex aryl alkyl ethers.

Authors+Show Affiliations

Department of Chemistry , University of Ulsan , 93 Daehak-Ro, Nam-Gu , Ulsan 44610 , Korea.Department of Chemistry , University of Ulsan , 93 Daehak-Ro, Nam-Gu , Ulsan 44610 , Korea.Department of Chemistry , University of Ulsan , 93 Daehak-Ro, Nam-Gu , Ulsan 44610 , Korea.

Pub Type(s)

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

Language

eng

PubMed ID

30226389

Citation

Khatun, Nilufa, et al. "Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents." Organic Letters, vol. 20, no. 19, 2018, pp. 6239-6243.
Khatun N, Kim MJ, Woo SK. Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents. Org Lett. 2018;20(19):6239-6243.
Khatun, N., Kim, M. J., & Woo, S. K. (2018). Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents. Organic Letters, 20(19), pp. 6239-6243. doi:10.1021/acs.orglett.8b02721.
Khatun N, Kim MJ, Woo SK. Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents. Org Lett. 2018 10 5;20(19):6239-6243. PubMed PMID: 30226389.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents. AU - Khatun,Nilufa, AU - Kim,Myeong Jun, AU - Woo,Sang Kook, Y1 - 2018/09/18/ PY - 2018/9/19/pubmed PY - 2018/9/19/medline PY - 2018/9/19/entrez SP - 6239 EP - 6243 JF - Organic letters JO - Org. Lett. VL - 20 IS - 19 N2 - A new neutral silicon-based traceless activation group (TAG) for visible-light photoredox-catalyzed hydroalkoxymethylation of alkenes is presented. This reaction involves in-situ-generated alkoxymethyl radical via single electron oxidation (SET) of α-TMS-substituted ethers, followed by subsequent conjugate addition to activated alkenes. Various functional groups were tolerated both under mild metal and metal-free conditions to provide good to excellent yields. Furthermore, the addition products were transformed to valuable synthetic building blocks, such as carboxylic acids, γ-butyrolactones, and complex aryl alkyl ethers. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/30226389/Visible_Light_Photoredox_Catalyzed_Hydroalkoxymethylation_of_Activated_Alkenes_Using_α_Silyl_Ethers_as_Alkoxymethyl_Radical_Equivalents_ L2 - https://dx.doi.org/10.1021/acs.orglett.8b02721 DB - PRIME DP - Unbound Medicine ER -