Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination

William E. Brenzovich; Diego Benitez; Aaron D. Lackner; Hunter P. Shunatona; Ekaterina Tkatchouk; William A. Goddard; F. Dean Toste

doi:10.1002/anie.201002739

Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination

William E. Brenzovich
, Diego Benitez
, Aaron D. Lackner
, Hunter P. Shunatona
, Ekaterina Tkatchouk
, William A. Goddard
, F. Dean Toste

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

Abstract

(Chemical equation presented) Gold-ilocks and the 3 mol% catalyst: Bimetallic gold bromides allow the room temperature aminoarylation of unactivated terminal olefins with aryl boronic acids using Selectfluor as an oxidant. A catalytic cycle involving gold (I)/gold(III) and a bimolecular reductive elimination for the key C-C bond-forming step is proposed, dppm= bis(diphenylphosphanyl) methane.

Original language	English
Pages (from-to)	5519-5522
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	32
DOIs	https://doi.org/10.1002/anie.201002739
Publication status	Published - 26 Jul 2010
Externally published	Yes

Keywords

Alkenes
C-c bond formation
Cyclization
Gold
Homogeneous catalysis

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10.1002/anie.201002739

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title = "Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination",

abstract = "(Chemical equation presented) Gold-ilocks and the 3 mol\% catalyst: Bimetallic gold bromides allow the room temperature aminoarylation of unactivated terminal olefins with aryl boronic acids using Selectfluor as an oxidant. A catalytic cycle involving gold (I)/gold(III) and a bimolecular reductive elimination for the key C-C bond-forming step is proposed, dppm= bis(diphenylphosphanyl) methane.",

keywords = "Alkenes, C-c bond formation, Cyclization, Gold, Homogeneous catalysis",

author = "Brenzovich, \{William E.\} and Diego Benitez and Lackner, \{Aaron D.\} and Shunatona, \{Hunter P.\} and Ekaterina Tkatchouk and Goddard, \{William A.\} and Toste, \{F. Dean\}",

year = "2010",

month = jul,

day = "26",

doi = "10.1002/anie.201002739",

language = "English",

volume = "49",

pages = "5519--5522",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

number = "32",

}

TY - JOUR

T1 - Gold-catalyzed intramolecular aminoarylation of alkenes

T2 - C-C bond formation through bimolecular reductive elimination

AU - Brenzovich, William E.

AU - Benitez, Diego

AU - Lackner, Aaron D.

AU - Shunatona, Hunter P.

AU - Tkatchouk, Ekaterina

AU - Goddard, William A.

AU - Toste, F. Dean

PY - 2010/7/26

Y1 - 2010/7/26

N2 - (Chemical equation presented) Gold-ilocks and the 3 mol% catalyst: Bimetallic gold bromides allow the room temperature aminoarylation of unactivated terminal olefins with aryl boronic acids using Selectfluor as an oxidant. A catalytic cycle involving gold (I)/gold(III) and a bimolecular reductive elimination for the key C-C bond-forming step is proposed, dppm= bis(diphenylphosphanyl) methane.

AB - (Chemical equation presented) Gold-ilocks and the 3 mol% catalyst: Bimetallic gold bromides allow the room temperature aminoarylation of unactivated terminal olefins with aryl boronic acids using Selectfluor as an oxidant. A catalytic cycle involving gold (I)/gold(III) and a bimolecular reductive elimination for the key C-C bond-forming step is proposed, dppm= bis(diphenylphosphanyl) methane.

KW - Alkenes

KW - C-c bond formation

KW - Cyclization

KW - Gold

KW - Homogeneous catalysis

UR - https://www.scopus.com/pages/publications/77955030369

U2 - 10.1002/anie.201002739

DO - 10.1002/anie.201002739

M3 - Article

C2 - 20602396

AN - SCOPUS:77955030369

SN - 1433-7851

VL - 49

SP - 5519

EP - 5522

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 32

ER -

Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination

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Keywords

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