Mechanistic Insight into the Catalytic Staudinger Ligation

Paul B White; Sjoerd J Rijpkema; Roderick P Bunschoten; Jasmin Mecinović

doi:10.1021/acs.orglett.8b04035

Mechanistic Insight into the Catalytic Staudinger Ligation

Paul B White
, Sjoerd J Rijpkema
, Roderick P Bunschoten
, Jasmin Mecinović

Institut for Fysik, Kemi og Farmaci

Radboud University Nijmegen

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

Abstract

Organophosphorus-catalyzed Staudinger ligation between carboxylic acids and azides in the presence of phenylsilane reductant produces amides. NMR-based mechanistic investigations revealed that the catalytic Staudinger ligation does not proceed via reduction of phosphine oxide but rather via reduction of iminophosphorane, which can subsequently undergo several transformations to produce the amide product.

Originalsprog	Engelsk
Tidsskrift	Organic Letters
Vol/bind	21
Udgave nummer	4
Sider (fra-til)	1011-1014
ISSN	1523-7060
DOI	https://doi.org/10.1021/acs.orglett.8b04035
Status	Udgivet - 15. feb. 2019

Dokumenter og links

10.1021/acs.orglett.8b04035

SDU link

Tjek adgangen til materialet i Syddansk Universitetsbiblioteks søgemaskine

Citationsformater

@article{9f8e84804b2645c480f91da9ac2de840,

title = "Mechanistic Insight into the Catalytic Staudinger Ligation",

abstract = "Organophosphorus-catalyzed Staudinger ligation between carboxylic acids and azides in the presence of phenylsilane reductant produces amides. NMR-based mechanistic investigations revealed that the catalytic Staudinger ligation does not proceed via reduction of phosphine oxide but rather via reduction of iminophosphorane, which can subsequently undergo several transformations to produce the amide product.",

author = "White, \{Paul B\} and Rijpkema, \{Sjoerd J\} and Bunschoten, \{Roderick P\} and Jasmin Mecinovi{\'c}",

year = "2019",

month = feb,

day = "15",

doi = "10.1021/acs.orglett.8b04035",

language = "English",

volume = "21",

pages = "1011--1014",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Mechanistic Insight into the Catalytic Staudinger Ligation

AU - White, Paul B

AU - Rijpkema, Sjoerd J

AU - Bunschoten, Roderick P

AU - Mecinović, Jasmin

PY - 2019/2/15

Y1 - 2019/2/15

N2 - Organophosphorus-catalyzed Staudinger ligation between carboxylic acids and azides in the presence of phenylsilane reductant produces amides. NMR-based mechanistic investigations revealed that the catalytic Staudinger ligation does not proceed via reduction of phosphine oxide but rather via reduction of iminophosphorane, which can subsequently undergo several transformations to produce the amide product.

AB - Organophosphorus-catalyzed Staudinger ligation between carboxylic acids and azides in the presence of phenylsilane reductant produces amides. NMR-based mechanistic investigations revealed that the catalytic Staudinger ligation does not proceed via reduction of phosphine oxide but rather via reduction of iminophosphorane, which can subsequently undergo several transformations to produce the amide product.

U2 - 10.1021/acs.orglett.8b04035

DO - 10.1021/acs.orglett.8b04035

M3 - Journal article

C2 - 30715895

SN - 1523-7060

VL - 21

SP - 1011

EP - 1014

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Mechanistic Insight into the Catalytic Staudinger Ligation

Abstract

Dokumenter og links

SDU link

Fingeraftryk

Citationsformater