Anti-Markovnikov Addition Reactions of Oxy-Acids to Alkenes Enabled by Photoredox Catalysis Public Deposited

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  • March 19, 2019
Creator
  • Hamilton, David
    • Affiliation: College of Arts and Sciences, Department of Chemistry
Abstract
  • The addition of nucleophiles to alkenes with complete anti-Markovnikov selectivity employing reagents in catalytic quantities has been a major challenge for the field of organic synthesis, and Past efforts employing primarily transition-metal catalysis have only partially solved this long-standing problem. This work describes the development of a novel two-component catalytic system comprised of a photoredox catalyst and a catalytic hydrogen-atom donor, which we have demonstrated to be capable of carrying out the addition of oxy-acids to alkenes with complete regioselectivity. Some rudimentary mechanistic experiments are included to highlight the importance of both catalytic species used in the system, and applications to the synthesis of cyclic ethers and lactones are detailed. Other noteworthy applications of this system are discussed, as are preliminary results for future applications of the detailed catalytic platform.
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  • In Copyright
Advisor
  • Templeton, Joseph
  • Alexanian, Erik
  • Forbes, Malcolm
  • Nicewicz, David
  • Brookhart, Maurice
Degree
  • Doctor of Philosophy
Degree granting institution
  • University of North Carolina at Chapel Hill Graduate School
Graduation year
  • 2014
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Place of publication
  • Chapel Hill, NC
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