Divergent Mechanistic Scenarios for the C−sp2 and C−sp3 C−H Insertion of Aurated Aryl Cations

Janina Bucher; Thomas Wurm; Kaveh Farshadfar; Michael Schukin; Georgios Uzunidis; Matthias Rudolph; Frank Rominger; Alireza Ariafard; A. Stephen K. Hashmi

doi:10.1002/adsc.202300548

Divergent Mechanistic Scenarios for the C−sp² and C−sp³ C−H Insertion of Aurated Aryl Cations

Janina Bucher, Thomas Wurm, Kaveh Farshadfar, Michael Schukin, Georgios Uzunidis, Matthias Rudolph, Frank Rominger, Alireza Ariafard, A. Stephen K. Hashmi^*

^*Tämän työn vastaava kirjoittaja

Tutkimustuotos: Lehtiartikkeli › Article › Scientific › vertaisarvioitu

4 Sitaatiot (Scopus)

19 Lataukset (Pure)

Abstrakti

By employing the sterically highly demanding steering ligand IPr* at a gold(I) center, it is possible to induce a 6-endo-dig cyclization pathway in 1,5-diynes bearing terminal alkyne moieties. The resulting aurated naphthyl cations are utilized for the intermolecular formation of C−C bonds via C−H insertion of aromatic and aliphatic C−H bonds. The mechanisms of these transformations were studied by quantum chemical calculations.

Alkuperäiskieli	Englanti
Sivut	3320-3327
Sivumäärä	8
Julkaisu	Advanced Synthesis and Catalysis
Vuosikerta	365
Numero	19
Varhainen verkossa julkaisun päivämäärä	23 elok. 2023
DOI - pysyväislinkit	https://doi.org/10.1002/adsc.202300548
Tila	Julkaistu - 13 lokak. 2023
OKM-julkaisutyyppi	A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Pääsy asiakirjaan

10.1002/adsc.202300548Lisenssi: CC BY-NC-ND

CHEM_Bucher_et_al_Divergent Mechanistic_2023_Adv_Synth_CatalFinal published version, 5,03 MBLisenssi: CC BY-NC-ND

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title = "Divergent Mechanistic Scenarios for the C−sp2 and C−sp3 C−H Insertion of Aurated Aryl Cations",

abstract = "By employing the sterically highly demanding steering ligand IPr* at a gold(I) center, it is possible to induce a 6-endo-dig cyclization pathway in 1,5-diynes bearing terminal alkyne moieties. The resulting aurated naphthyl cations are utilized for the intermolecular formation of C−C bonds via C−H insertion of aromatic and aliphatic C−H bonds. The mechanisms of these transformations were studied by quantum chemical calculations.",

keywords = "aryl cations, C−H insertion, diynes, gold catalysis, high energy intermediates",

author = "Janina Bucher and Thomas Wurm and Kaveh Farshadfar and Michael Schukin and Georgios Uzunidis and Matthias Rudolph and Frank Rominger and Alireza Ariafard and Hashmi, {A. Stephen K.}",

note = "Funding Information: J. Bucher is grateful for a Chemiefonds scholarship of the Fonds der Chemischen Industrie. The authors thank Umicore AG & Co. KG for the generous donation of gold salts. Publisher Copyright: {\textcopyright} 2023 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH.",

year = "2023",

month = oct,

day = "13",

doi = "10.1002/adsc.202300548",

language = "English",

volume = "365",

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T1 - Divergent Mechanistic Scenarios for the C−sp2 and C−sp3 C−H Insertion of Aurated Aryl Cations

AU - Bucher, Janina

AU - Wurm, Thomas

AU - Farshadfar, Kaveh

AU - Schukin, Michael

AU - Uzunidis, Georgios

AU - Rudolph, Matthias

AU - Rominger, Frank

AU - Ariafard, Alireza

AU - Hashmi, A. Stephen K.

N1 - Funding Information: J. Bucher is grateful for a Chemiefonds scholarship of the Fonds der Chemischen Industrie. The authors thank Umicore AG & Co. KG for the generous donation of gold salts. Publisher Copyright: © 2023 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH.

PY - 2023/10/13

Y1 - 2023/10/13

N2 - By employing the sterically highly demanding steering ligand IPr* at a gold(I) center, it is possible to induce a 6-endo-dig cyclization pathway in 1,5-diynes bearing terminal alkyne moieties. The resulting aurated naphthyl cations are utilized for the intermolecular formation of C−C bonds via C−H insertion of aromatic and aliphatic C−H bonds. The mechanisms of these transformations were studied by quantum chemical calculations.

AB - By employing the sterically highly demanding steering ligand IPr* at a gold(I) center, it is possible to induce a 6-endo-dig cyclization pathway in 1,5-diynes bearing terminal alkyne moieties. The resulting aurated naphthyl cations are utilized for the intermolecular formation of C−C bonds via C−H insertion of aromatic and aliphatic C−H bonds. The mechanisms of these transformations were studied by quantum chemical calculations.

KW - aryl cations

KW - C−H insertion

KW - diynes

KW - gold catalysis

KW - high energy intermediates

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