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Radical Addition of Thiols to Oxa(aza)bicyclic Alkenes in Water

Publication ,  Journal Article
Yao, Y; Yang, W; Wang, C; Gu, F; Yang, D
Published in: Asian Journal of Organic Chemistry
April 1, 2019

An air-promoted radical addition reaction of various thiols to oxa(aza)bicyclic alkenes is reported, leading to the corresponding exo adducts in good to excellent yields (up to 99%) in water without the use of any metal catalyst, photoredox catalyst or radical initiator reagent under mild conditions. The reaction has a wide scopeof oxa(aza)bicyclic alkenes and thiols, which provides an easy and clean way for the direct preparation of thioethers. A proposed mechanism of an exo free radical attacking the double bond of an oxa(aza)bicyclic alkene was investigated by DFT calculations of stepwise reaction pathways and control experiments.

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Published In

Asian Journal of Organic Chemistry

DOI

ISSN

2193-5807

Publication Date

April 1, 2019

Volume

8

Issue

4

Start / End Page

506 / 513

Related Subject Headings

  • 3405 Organic chemistry
  • 0305 Organic Chemistry
 

Citation

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Yao, Y., Yang, W., Wang, C., Gu, F., & Yang, D. (2019). Radical Addition of Thiols to Oxa(aza)bicyclic Alkenes in Water. Asian Journal of Organic Chemistry, 8(4), 506–513. https://doi.org/10.1002/ajoc.201900033
Yao, Y., W. Yang, C. Wang, F. Gu, and D. Yang. “Radical Addition of Thiols to Oxa(aza)bicyclic Alkenes in Water.” Asian Journal of Organic Chemistry 8, no. 4 (April 1, 2019): 506–13. https://doi.org/10.1002/ajoc.201900033.
Yao Y, Yang W, Wang C, Gu F, Yang D. Radical Addition of Thiols to Oxa(aza)bicyclic Alkenes in Water. Asian Journal of Organic Chemistry. 2019 Apr 1;8(4):506–13.
Yao, Y., et al. “Radical Addition of Thiols to Oxa(aza)bicyclic Alkenes in Water.” Asian Journal of Organic Chemistry, vol. 8, no. 4, Apr. 2019, pp. 506–13. Scopus, doi:10.1002/ajoc.201900033.
Yao Y, Yang W, Wang C, Gu F, Yang D. Radical Addition of Thiols to Oxa(aza)bicyclic Alkenes in Water. Asian Journal of Organic Chemistry. 2019 Apr 1;8(4):506–513.
Journal cover image

Published In

Asian Journal of Organic Chemistry

DOI

ISSN

2193-5807

Publication Date

April 1, 2019

Volume

8

Issue

4

Start / End Page

506 / 513

Related Subject Headings

  • 3405 Organic chemistry
  • 0305 Organic Chemistry