Silver Effect in Regiodivergent Gold-Catalyzed Hydroaminations

Marcos Veguillas; Georgina M. Rosair; Magnus W.P. Bebbington; Ai Lan Lee

doi:10.1021/acscatal.9b00249

Silver Effect in Regiodivergent Gold-Catalyzed Hydroaminations

Marcos Veguillas, Georgina M. Rosair, Magnus W.P. Bebbington, Ai Lan Lee

Chemistry and Biochemistry

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

28 Scopus citations

Abstract

We report a silver-induced switching of regioselectivity in gold-catalyzed reactions, and we provide mechanistic evidence to suggest a true "silver effect": that is, one that is implicated in the catalytic process itself, via σ-gold π-silver acetylides. These results are of significance because they clearly show that the use of silver as halide abstractors in gold-catalyzed reactions may result in "silver effects" when terminal alkyne substrates are involved.

Original language	English
Pages (from-to)	2552-2557
Number of pages	6
Journal	ACS Catalysis
Volume	9
Issue number	3
DOIs	https://doi.org/10.1021/acscatal.9b00249
State	Published - 1 Mar 2019

Keywords

digold
gold
gold acetylide
hydroamination
regiodivergent
silver
silver-effect

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10.1021/acscatal.9b00249

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@article{d57017e7b4424620910ac6cf92aaf153,

title = "Silver Effect in Regiodivergent Gold-Catalyzed Hydroaminations",

abstract = "We report a silver-induced switching of regioselectivity in gold-catalyzed reactions, and we provide mechanistic evidence to suggest a true {"}silver effect{"}: that is, one that is implicated in the catalytic process itself, via σ-gold π-silver acetylides. These results are of significance because they clearly show that the use of silver as halide abstractors in gold-catalyzed reactions may result in {"}silver effects{"} when terminal alkyne substrates are involved.",

keywords = "digold, gold, gold acetylide, hydroamination, regiodivergent, silver, silver-effect",

author = "Marcos Veguillas and Rosair, \{Georgina M.\} and Bebbington, \{Magnus W.P.\} and Lee, \{Ai Lan\}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = mar,

day = "1",

doi = "10.1021/acscatal.9b00249",

language = "English",

volume = "9",

pages = "2552--2557",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Silver Effect in Regiodivergent Gold-Catalyzed Hydroaminations

AU - Veguillas, Marcos

AU - Rosair, Georgina M.

AU - Bebbington, Magnus W.P.

AU - Lee, Ai Lan

PY - 2019/3/1

Y1 - 2019/3/1

N2 - We report a silver-induced switching of regioselectivity in gold-catalyzed reactions, and we provide mechanistic evidence to suggest a true "silver effect": that is, one that is implicated in the catalytic process itself, via σ-gold π-silver acetylides. These results are of significance because they clearly show that the use of silver as halide abstractors in gold-catalyzed reactions may result in "silver effects" when terminal alkyne substrates are involved.

AB - We report a silver-induced switching of regioselectivity in gold-catalyzed reactions, and we provide mechanistic evidence to suggest a true "silver effect": that is, one that is implicated in the catalytic process itself, via σ-gold π-silver acetylides. These results are of significance because they clearly show that the use of silver as halide abstractors in gold-catalyzed reactions may result in "silver effects" when terminal alkyne substrates are involved.

KW - digold

KW - gold

KW - gold acetylide

KW - hydroamination

KW - regiodivergent

KW - silver

KW - silver-effect

UR - https://www.scopus.com/pages/publications/85062341921

U2 - 10.1021/acscatal.9b00249

DO - 10.1021/acscatal.9b00249

M3 - Article

AN - SCOPUS:85062341921

SN - 2155-5435

VL - 9

SP - 2552

EP - 2557

JO - ACS Catalysis

JF - ACS Catalysis

IS - 3

ER -

Silver Effect in Regiodivergent Gold-Catalyzed Hydroaminations

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Keywords

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