Factors Controlling Reactivity in the Hydrogen Atom Transfer and Radical Addition Steps of a Radical Relay Cascade

Yike Zou; Xiao-Song Xue; Yifan Deng; Amos B Smith 3rd; K N Houk

doi:10.1021/acs.orglett.9b02023

Factors Controlling Reactivity in the Hydrogen Atom Transfer and Radical Addition Steps of a Radical Relay Cascade

Org Lett. 2019 Aug 2;21(15):5894-5897. doi: 10.1021/acs.orglett.9b02023. Epub 2019 Jul 15.

Authors

Yike Zou¹, Xiao-Song Xue¹, Yifan Deng², Amos B Smith 3rd², K N Houk¹

Affiliations

¹ Department of Chemistry and Biochemistry , University of California , Los Angeles , California 90095-1569 , United States.
² Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104 , United States.

Abstract

DFT exploration of 1,5- and 1,6-hydrogen atom transfers (HAT), radical addition, and relay to alkene is reported. The reactivity of 1,5- and 1,6-HAT are similar. We also explored reactions involving a multiple radical transferring process. Initially generated radicals undergo a multiple HAT process to form multiple bonds in a "relay" fashion, provided by exquisitely balanced rates.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Hydrogen / chemistry*
Hydrogen Bonding
Kinetics

Substances

Hydrogen

Grants and funding

R01 GM109078/GM/NIGMS NIH HHS/United States