Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts: Redox Gold Catalysis without an External Oxidant

Rong Cai; Mei Lu; Ellen Y. Aguilera; Yumeng Xi; Novruz G. Akhmedov; Jeffrey L. Petersen; Hao Chen; Xiaodong Shi

doi:10.1002/anie.201503546

Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts: Redox Gold Catalysis without an External Oxidant

Rong Cai, Mei Lu, Ellen Y. Aguilera, Yumeng Xi, Novruz G. Akhmedov, Jeffrey L. Petersen, Hao Chen, Xiaodong Shi

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

123 Scopus citations

Abstract

Gold-catalyzed C(sp)-C(sp²) and C(sp²)-C(sp²) cross-coupling reactions are accomplished with aryldiazonium salts as the coupling partner. With the assistance of bpy ligand, gold(I) species were oxidized to gold(III) by diazonium without any external oxidants. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the nitrogen extrusion followed by Au^III reductive elimination as the key step.

Original language	English (US)
Pages (from-to)	8772-8776
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	30
DOIs	https://doi.org/10.1002/anie.201503546
State	Published - Jul 20 2015
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

Keywords

aryldiazonium salt
cross-coupling
gold
redox catalysis

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10.1002/anie.201503546

Cite this

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title = "Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts: Redox Gold Catalysis without an External Oxidant",

abstract = "Gold-catalyzed C(sp)-C(sp2) and C(sp2)-C(sp2) cross-coupling reactions are accomplished with aryldiazonium salts as the coupling partner. With the assistance of bpy ligand, gold(I) species were oxidized to gold(III) by diazonium without any external oxidants. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the nitrogen extrusion followed by AuIII reductive elimination as the key step.",

keywords = "aryldiazonium salt, cross-coupling, gold, redox catalysis",

author = "Rong Cai and Mei Lu and Aguilera, {Ellen Y.} and Yumeng Xi and Akhmedov, {Novruz G.} and Petersen, {Jeffrey L.} and Hao Chen and Xiaodong Shi",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

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day = "20",

doi = "10.1002/anie.201503546",

language = "English (US)",

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TY - JOUR

T1 - Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts

T2 - Redox Gold Catalysis without an External Oxidant

AU - Cai, Rong

AU - Lu, Mei

AU - Aguilera, Ellen Y.

AU - Xi, Yumeng

AU - Akhmedov, Novruz G.

AU - Petersen, Jeffrey L.

AU - Chen, Hao

AU - Shi, Xiaodong

PY - 2015/7/20

Y1 - 2015/7/20

N2 - Gold-catalyzed C(sp)-C(sp2) and C(sp2)-C(sp2) cross-coupling reactions are accomplished with aryldiazonium salts as the coupling partner. With the assistance of bpy ligand, gold(I) species were oxidized to gold(III) by diazonium without any external oxidants. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the nitrogen extrusion followed by AuIII reductive elimination as the key step.

AB - Gold-catalyzed C(sp)-C(sp2) and C(sp2)-C(sp2) cross-coupling reactions are accomplished with aryldiazonium salts as the coupling partner. With the assistance of bpy ligand, gold(I) species were oxidized to gold(III) by diazonium without any external oxidants. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the nitrogen extrusion followed by AuIII reductive elimination as the key step.

KW - aryldiazonium salt

KW - cross-coupling

KW - gold

KW - redox catalysis

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M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts: Redox Gold Catalysis without an External Oxidant

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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