ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
3 files

Tethered Silanoxyiodination of Alkenes

preprint
submitted on 01.04.2021, 22:28 and posted on 02.04.2021, 13:14 by Ranjeet Dhokale, Frederick Seidl, Anand H. Shinde, Joel T Mague, Shyam Sathyamoorthi
We present the first examples of tethered silanoxyiodination reactions of allylic alcohols. The products are useful
silanediol organoiodide synthons and are formed with high regioselectivity and diastereocontrol. The reaction is scalable greater than 10-fold without loss of yield or selectivity. Furthermore, the products are starting materials for further transformations, including de-iodination, C–N bond installation, epoxide synthesis, and de-silylation. DFT calculations provide a basis for understanding the exquisite 6-endo selectivity of this silanoxyiodination reaction and show that the observed products are both kinetically and thermodynamically preferred.

History

Email Address of Submitting Author

ssathyam@ku.edu

Institution

University of Kansas

Country

United States

ORCID For Submitting Author

0000-0003-4705-7349

Declaration of Conflict of Interest

None

Exports

ChemRxiv

Exports