Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen-RadicalsCitation formats

  • Authors:
  • Sara Morcillo
  • Elizabeth Dauncey
  • Ji Hye Kim
  • James J. Douglas
  • Nadeem S Sheikh
  • And 1 others
  • External authors:
  • Daniele Leonori

Standard

Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen-Radicals. / Morcillo, Sara; Dauncey, Elizabeth; Kim, Ji Hye; Douglas, James J. ; Sheikh, Nadeem S; Leonori, Daniele.

In: Angewandte Chemie - International Edition, Vol. 57, No. 39, 19.09.2018, p. 12945-12949.

Research output: Contribution to journalArticle

Harvard

Morcillo, S, Dauncey, E, Kim, JH, Douglas, JJ, Sheikh, NS & Leonori, D 2018, 'Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen-Radicals', Angewandte Chemie - International Edition, vol. 57, no. 39, pp. 12945-12949. https://doi.org/10.1002/anie.201807941

APA

Morcillo, S., Dauncey, E., Kim, J. H., Douglas, J. J., Sheikh, N. S., & Leonori, D. (2018). Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen-Radicals. Angewandte Chemie - International Edition, 57(39), 12945-12949. https://doi.org/10.1002/anie.201807941

Vancouver

Morcillo S, Dauncey E, Kim JH, Douglas JJ, Sheikh NS, Leonori D. Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen-Radicals. Angewandte Chemie - International Edition. 2018 Sep 19;57(39):12945-12949. https://doi.org/10.1002/anie.201807941

Author

Morcillo, Sara ; Dauncey, Elizabeth ; Kim, Ji Hye ; Douglas, James J. ; Sheikh, Nadeem S ; Leonori, Daniele. / Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen-Radicals. In: Angewandte Chemie - International Edition. 2018 ; Vol. 57, No. 39. pp. 12945-12949.

Bibtex

@article{b4c9dd520bb74e95a1571ff082881e23,
title = "Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen-Radicals",
abstract = "The selective functionalization of C(sp3)−H bonds at distal positions to functional groups is a challenging task in synthetic chemistry. Reported here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5‐H‐atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant of most common functional groups and delivers useful building blocks that can be further elaborated. The utility of this strategy is demonstrated through the late‐stage functionalization of amino acids and a dipeptide.",
author = "Sara Morcillo and Elizabeth Dauncey and Kim, {Ji Hye} and Douglas, {James J.} and Sheikh, {Nadeem S} and Daniele Leonori",
year = "2018",
month = "9",
day = "19",
doi = "10.1002/anie.201807941",
language = "English",
volume = "57",
pages = "12945--12949",
journal = "Angewandte Chemie, International Edition",
issn = "1433-7851",
publisher = "John Wiley & Sons Ltd",
number = "39",

}

RIS

TY - JOUR

T1 - Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen-Radicals

AU - Morcillo, Sara

AU - Dauncey, Elizabeth

AU - Kim, Ji Hye

AU - Douglas, James J.

AU - Sheikh, Nadeem S

AU - Leonori, Daniele

PY - 2018/9/19

Y1 - 2018/9/19

N2 - The selective functionalization of C(sp3)−H bonds at distal positions to functional groups is a challenging task in synthetic chemistry. Reported here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5‐H‐atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant of most common functional groups and delivers useful building blocks that can be further elaborated. The utility of this strategy is demonstrated through the late‐stage functionalization of amino acids and a dipeptide.

AB - The selective functionalization of C(sp3)−H bonds at distal positions to functional groups is a challenging task in synthetic chemistry. Reported here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5‐H‐atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant of most common functional groups and delivers useful building blocks that can be further elaborated. The utility of this strategy is demonstrated through the late‐stage functionalization of amino acids and a dipeptide.

U2 - 10.1002/anie.201807941

DO - 10.1002/anie.201807941

M3 - Article

VL - 57

SP - 12945

EP - 12949

JO - Angewandte Chemie, International Edition

JF - Angewandte Chemie, International Edition

SN - 1433-7851

IS - 39

ER -