Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization CascadesCitation formats

  • Authors:
  • Lucrezia Angelini
  • Jacob Davies
  • Marco Simonetti
  • Laia Malet Sanz
  • Nadeem S. Sheikh
  • And 1 others
  • External authors:
  • Daniele Leonori

Standard

Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades. / Angelini, Lucrezia; Davies, Jacob; Simonetti, Marco; Malet Sanz, Laia; Sheikh, Nadeem S.; Leonori, Daniele.

In: Angewandte Chemie International Edition, Vol. 58, No. 15, 2019, p. 5003-5007.

Research output: Contribution to journalArticle

Harvard

Angelini, L, Davies, J, Simonetti, M, Malet Sanz, L, Sheikh, NS & Leonori, D 2019, 'Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades', Angewandte Chemie International Edition, vol. 58, no. 15, pp. 5003-5007. https://doi.org/10.1002/anie.201900510

APA

Angelini, L., Davies, J., Simonetti, M., Malet Sanz, L., Sheikh, N. S., & Leonori, D. (2019). Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades. Angewandte Chemie International Edition, 58(15), 5003-5007. https://doi.org/10.1002/anie.201900510

Vancouver

Angelini L, Davies J, Simonetti M, Malet Sanz L, Sheikh NS, Leonori D. Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades. Angewandte Chemie International Edition. 2019;58(15):5003-5007. https://doi.org/10.1002/anie.201900510

Author

Angelini, Lucrezia ; Davies, Jacob ; Simonetti, Marco ; Malet Sanz, Laia ; Sheikh, Nadeem S. ; Leonori, Daniele. / Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades. In: Angewandte Chemie International Edition. 2019 ; Vol. 58, No. 15. pp. 5003-5007.

Bibtex

@article{7c9f594edd954bdfb9941e408e5edfee,
title = "Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades",
abstract = "Here we report a strategy for the generation of nitrogen‐radicals by ground‐state single electron transfer with organyl‐Ni(I) species. Depending on the philicity of the N‐radical, two types of processes have been developed. In the case of nucleophilic aminyl radicals direct N‐arylation with aryl organozinc, organoboron and organosilicon reagents was achieved. In the case of electrophilic amidyl radicals, cascade processes involving intramolecular cyclization, followed by reaction with both aryl and alkyl organometallics have been developed. The N‐cyclization‐alkylation cascade introduces a novel retrosynthetic disconnection for the assembly of substituted lactams and pyrrolidines with its potential demonstrated in the short total synthesis of four venom alkaloids.",
keywords = "alkaloid, arylation, nitrogen radicals, radical cyclization, single electron transfer",
author = "Lucrezia Angelini and Jacob Davies and Marco Simonetti and {Malet Sanz}, Laia and Sheikh, {Nadeem S.} and Daniele Leonori",
year = "2019",
doi = "10.1002/anie.201900510",
language = "English",
volume = "58",
pages = "5003--5007",
journal = "Angewandte Chemie, International Edition",
issn = "1433-7851",
publisher = "John Wiley & Sons Ltd",
number = "15",

}

RIS

TY - JOUR

T1 - Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades

AU - Angelini, Lucrezia

AU - Davies, Jacob

AU - Simonetti, Marco

AU - Malet Sanz, Laia

AU - Sheikh, Nadeem S.

AU - Leonori, Daniele

PY - 2019

Y1 - 2019

N2 - Here we report a strategy for the generation of nitrogen‐radicals by ground‐state single electron transfer with organyl‐Ni(I) species. Depending on the philicity of the N‐radical, two types of processes have been developed. In the case of nucleophilic aminyl radicals direct N‐arylation with aryl organozinc, organoboron and organosilicon reagents was achieved. In the case of electrophilic amidyl radicals, cascade processes involving intramolecular cyclization, followed by reaction with both aryl and alkyl organometallics have been developed. The N‐cyclization‐alkylation cascade introduces a novel retrosynthetic disconnection for the assembly of substituted lactams and pyrrolidines with its potential demonstrated in the short total synthesis of four venom alkaloids.

AB - Here we report a strategy for the generation of nitrogen‐radicals by ground‐state single electron transfer with organyl‐Ni(I) species. Depending on the philicity of the N‐radical, two types of processes have been developed. In the case of nucleophilic aminyl radicals direct N‐arylation with aryl organozinc, organoboron and organosilicon reagents was achieved. In the case of electrophilic amidyl radicals, cascade processes involving intramolecular cyclization, followed by reaction with both aryl and alkyl organometallics have been developed. The N‐cyclization‐alkylation cascade introduces a novel retrosynthetic disconnection for the assembly of substituted lactams and pyrrolidines with its potential demonstrated in the short total synthesis of four venom alkaloids.

KW - alkaloid

KW - arylation

KW - nitrogen radicals

KW - radical cyclization

KW - single electron transfer

U2 - 10.1002/anie.201900510

DO - 10.1002/anie.201900510

M3 - Article

VL - 58

SP - 5003

EP - 5007

JO - Angewandte Chemie, International Edition

JF - Angewandte Chemie, International Edition

SN - 1433-7851

IS - 15

ER -