Visible-light-mediated, nitrogen-centered radical amination of tertiary alkyl halides under metal-free conditions to form α-tertiary amines.
A mild and operationally convenient amino-functionalization of a range of tertiary alkyl halides by reaction with iminoiodinanes (PhI[double bond, length as m-dash]NNs) and I2 has been developed. According to the mechanistic experiments described within, the reaction is speculated to proceed through a light-promoted, N-centered radical pathway involving a N,N-diiodosulfonamide reactive species. This method of direct N-incorporation offers an attractive alternative to the production of α-tertiary amines, a synthetically challenging structural class found in a variety of bioactive molecules.
Department of Chemistry, Hanover College, 484 Ball Drive, Hanover, Indiana 47243, USA.
Alexander C
AC
Brueckner
Department of Chemistry, Hanover College, 484 Ball Drive, Hanover, Indiana 47243, USA.
Erin N
EN
Hancock
Department of Chemistry, Hanover College, 484 Ball Drive, Hanover, Indiana 47243, USA.
Evan J
EJ
Anders
Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, Oklahoma 74104, USA. angus-lamar@utulsa.edu.
Matthew M
MM
Tierney
Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, Oklahoma 74104, USA. angus-lamar@utulsa.edu.
Heather R
HR
Morgan
Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, Oklahoma 74104, USA. angus-lamar@utulsa.edu.
Kristina A
KA
Scott
Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, Oklahoma 74104, USA. angus-lamar@utulsa.edu.
Angus A
AA
Lamar