An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence

Miles H. Aukland; Fabien J. T. Talbot; José A. Fernández-salas; Matthew Ball; Alexander P. Pulis; David J. Procter

doi:10.1002/anie.201805396

An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence

Miles H. Aukland, Fabien J. T. Talbot, José A. Fernández-salas, Matthew Ball, Alexander P. Pulis, David J. Procter

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Abstract

An interrupted Pummerer/nickel‐catalysed cross‐coupling strategy has been developed and used in the elaboration of styrenes. The operationally simple method can be carried out as a one‐pot process, involves the direct formation of stable alkenyl sulfonium salt intermediates, utilises a commercially available sulfoxide, catalyst, and ligand, operates at ambient temperature, accommodates sp‐, sp²‐, and sp³‐hybridised organozinc coupling partners, and delivers functionalised styrene products in high yields over two steps. An interrupted Pummerer/cyclisation approach has also been used to access carbo‐ and heterocyclic alkenyl sulfonium salts for cross‐coupling.

Original language	English
Journal	Angewandte Chemie International Edition
Volume	57
Issue number	31
Early online date	8 Jun 2018
DOIs	https://doi.org/10.1002/anie.201805396
Publication status	Published - 26 Jul 2018

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DJP-Accepted-manuscript-June8Accepted author manuscript, 1.74 MB

CCDC 1836658: Experimental Crystal Structure Determination
Aukland, M. (Contributor), Talbot, F. (Contributor), Fernández-salas, J. A. (Contributor), Ball, M. (Contributor), Pulis, A. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2018
DOI: 10.5517/ccdc.csd.cc1zn61w, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1zn61w&sid=DataCite
Dataset
CCDC 1832463: Experimental Crystal Structure Determination
Aukland, M. (Contributor), Talbot, F. (Contributor), Fernández-salas, J. A. (Contributor), Ball, M. (Contributor), Pulis, A. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2018
DOI: 10.5517/ccdc.csd.cc1zhtq0, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1zhtq0&sid=DataCite
Dataset
CCDC 1832462: Experimental Crystal Structure Determination
Aukland, M. (Contributor), Talbot, F. (Contributor), Fernández-salas, J. A. (Contributor), Ball, M. (Contributor), Pulis, A. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2018
DOI: 10.5517/ccdc.csd.cc1zhtpz, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1zhtpz&sid=DataCite
Dataset

Cite this

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title = "An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence",

abstract = "An interrupted Pummerer/nickel‐catalysed cross‐coupling strategy has been developed and used in the elaboration of styrenes. The operationally simple method can be carried out as a one‐pot process, involves the direct formation of stable alkenyl sulfonium salt intermediates, utilises a commercially available sulfoxide, catalyst, and ligand, operates at ambient temperature, accommodates sp‐, sp2‐, and sp3‐hybridised organozinc coupling partners, and delivers functionalised styrene products in high yields over two steps. An interrupted Pummerer/cyclisation approach has also been used to access carbo‐ and heterocyclic alkenyl sulfonium salts for cross‐coupling.",

author = "Aukland, {Miles H.} and Talbot, {Fabien J. T.} and Fern{\'a}ndez-salas, {Jos{\'e} A.} and Matthew Ball and Pulis, {Alexander P.} and Procter, {David J.}",

year = "2018",

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doi = "10.1002/anie.201805396",

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T1 - An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence

AU - Aukland, Miles H.

AU - Talbot, Fabien J. T.

AU - Fernández-salas, José A.

AU - Ball, Matthew

AU - Pulis, Alexander P.

AU - Procter, David J.

PY - 2018/7/26

Y1 - 2018/7/26

N2 - An interrupted Pummerer/nickel‐catalysed cross‐coupling strategy has been developed and used in the elaboration of styrenes. The operationally simple method can be carried out as a one‐pot process, involves the direct formation of stable alkenyl sulfonium salt intermediates, utilises a commercially available sulfoxide, catalyst, and ligand, operates at ambient temperature, accommodates sp‐, sp2‐, and sp3‐hybridised organozinc coupling partners, and delivers functionalised styrene products in high yields over two steps. An interrupted Pummerer/cyclisation approach has also been used to access carbo‐ and heterocyclic alkenyl sulfonium salts for cross‐coupling.

AB - An interrupted Pummerer/nickel‐catalysed cross‐coupling strategy has been developed and used in the elaboration of styrenes. The operationally simple method can be carried out as a one‐pot process, involves the direct formation of stable alkenyl sulfonium salt intermediates, utilises a commercially available sulfoxide, catalyst, and ligand, operates at ambient temperature, accommodates sp‐, sp2‐, and sp3‐hybridised organozinc coupling partners, and delivers functionalised styrene products in high yields over two steps. An interrupted Pummerer/cyclisation approach has also been used to access carbo‐ and heterocyclic alkenyl sulfonium salts for cross‐coupling.

U2 - 10.1002/anie.201805396

DO - 10.1002/anie.201805396

M3 - Article

VL - 57

JO - Angewandte Chemie. International Edition

JF - Angewandte Chemie. International Edition

SN - 1433-7851

IS - 31

ER -

An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence

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Datasets

CCDC 1836658: Experimental Crystal Structure Determination

CCDC 1832463: Experimental Crystal Structure Determination

CCDC 1832462: Experimental Crystal Structure Determination

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