M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines

Vlada Vershinin; Doron Pappo

doi:10.1021/acs.orglett.0c00296

M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines

Vlada Vershinin, Doron Pappo

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

Iron- A nd manganese-catalyzed para-selective oxidative amination of (4-R)phenols by primary and secondary anilines was developed. Depending on the identity of the R group, the products of this efficient reaction are either benzoquinone anils (C-N coupling) that are produced via a sequential oxidative amination/dehydrogenation (R = H), oxidative amination/elimination (R = OMe) steps, or N,O-biaryl compounds (C-C coupling) that are formed when R = alkyl through an oxidative amination/[3,3]-sigmatropic rearrangement (quinamine rearrangement) process.

Original language	English
Pages (from-to)	1941-1946
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.0c00296
State	Published - 6 Mar 2020

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.0c00296

Cite this

@article{d13dfdbd51cc463eb3b7a38f7ea0964c,

title = "M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines",

abstract = "Iron- A nd manganese-catalyzed para-selective oxidative amination of (4-R)phenols by primary and secondary anilines was developed. Depending on the identity of the R group, the products of this efficient reaction are either benzoquinone anils (C-N coupling) that are produced via a sequential oxidative amination/dehydrogenation (R = H), oxidative amination/elimination (R = OMe) steps, or N,O-biaryl compounds (C-C coupling) that are formed when R = alkyl through an oxidative amination/[3,3]-sigmatropic rearrangement (quinamine rearrangement) process.",

author = "Vlada Vershinin and Doron Pappo",

note = "Funding Information: This work was supported by the Israel Science Foundation (Grant No. 164/16). Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = mar,

day = "6",

doi = "10.1021/acs.orglett.0c00296",

language = "English",

volume = "22",

pages = "1941--1946",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines

AU - Vershinin, Vlada

AU - Pappo, Doron

PY - 2020/3/6

Y1 - 2020/3/6

N2 - Iron- A nd manganese-catalyzed para-selective oxidative amination of (4-R)phenols by primary and secondary anilines was developed. Depending on the identity of the R group, the products of this efficient reaction are either benzoquinone anils (C-N coupling) that are produced via a sequential oxidative amination/dehydrogenation (R = H), oxidative amination/elimination (R = OMe) steps, or N,O-biaryl compounds (C-C coupling) that are formed when R = alkyl through an oxidative amination/[3,3]-sigmatropic rearrangement (quinamine rearrangement) process.

AB - Iron- A nd manganese-catalyzed para-selective oxidative amination of (4-R)phenols by primary and secondary anilines was developed. Depending on the identity of the R group, the products of this efficient reaction are either benzoquinone anils (C-N coupling) that are produced via a sequential oxidative amination/dehydrogenation (R = H), oxidative amination/elimination (R = OMe) steps, or N,O-biaryl compounds (C-C coupling) that are formed when R = alkyl through an oxidative amination/[3,3]-sigmatropic rearrangement (quinamine rearrangement) process.

UR - http://www.scopus.com/inward/record.url?scp=85081944042&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c00296

DO - 10.1021/acs.orglett.0c00296

M3 - Article

C2 - 32049535

AN - SCOPUS:85081944042

SN - 1523-7060

VL - 22

SP - 1941

EP - 1946

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this