Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis

Adrian Tlahuext-Aca; Sarah Yunmi Lee; Shu Sakamoto; John F. Hartwig

doi:10.1021/acscatal.0c05254

Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis

Adrian Tlahuext-Aca, Sarah Yunmi Lee, Shu Sakamoto, John F. Hartwig

Department of Chemistry

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

20 Citations (Scopus)

Abstract

The direct, catalytic arylation of simple arenes in small excess with aryl bromides is disclosed. The developed method does not require the assistance of directing groups and relies on a synergistic catalytic cycle in which phosphine-ligated silver complexes cleave the aryl C-H bond, while palladium catalysts enable the formation of the biaryl products. Mechanistic experiments, including kinetic isotope effects, competition experiments, and hydrogen-deuterium exchange, support a catalytic cycle in which cleavage of the C-H bond by silver is the rate-determining step.

Original language	English
Pages (from-to)	1430-1434
Number of pages	5
Journal	ACS Catalysis
Volume	11
Issue number	3
DOIs	https://doi.org/10.1021/acscatal.0c05254
Publication status	Published - 2021 Feb 5

Bibliographical note

Funding Information:
We gratefully acknowledge financial support from the NIH (R35 GM130387 to J.F.H. and F32-GM113404 to S.Y.L.). We thank the College of Chemistry’s NMR facility for resources provided and the staff for their assistance. Instruments in CoC-NMR are supported in part by the NIH (S10OD024998). A.T.A Thanks UC MEXUS-CONACYT for a Postdoctoral Research Fellowship.

Publisher Copyright:
©

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

Access to Document

10.1021/acscatal.0c05254

Cite this

@article{00c9eb6d92704994a9163fc905d3dcb9,

title = "Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis",

abstract = "The direct, catalytic arylation of simple arenes in small excess with aryl bromides is disclosed. The developed method does not require the assistance of directing groups and relies on a synergistic catalytic cycle in which phosphine-ligated silver complexes cleave the aryl C-H bond, while palladium catalysts enable the formation of the biaryl products. Mechanistic experiments, including kinetic isotope effects, competition experiments, and hydrogen-deuterium exchange, support a catalytic cycle in which cleavage of the C-H bond by silver is the rate-determining step.",

author = "Adrian Tlahuext-Aca and Lee, {Sarah Yunmi} and Shu Sakamoto and Hartwig, {John F.}",

note = "Funding Information: We gratefully acknowledge financial support from the NIH (R35 GM130387 to J.F.H. and F32-GM113404 to S.Y.L.). We thank the College of Chemistry{\textquoteright}s NMR facility for resources provided and the staff for their assistance. Instruments in CoC-NMR are supported in part by the NIH (S10OD024998). A.T.A Thanks UC MEXUS-CONACYT for a Postdoctoral Research Fellowship. Publisher Copyright: {\textcopyright} ",

year = "2021",

month = feb,

day = "5",

doi = "10.1021/acscatal.0c05254",

language = "English",

volume = "11",

pages = "1430--1434",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis

AU - Tlahuext-Aca, Adrian

AU - Lee, Sarah Yunmi

AU - Sakamoto, Shu

AU - Hartwig, John F.

N1 - Funding Information: We gratefully acknowledge financial support from the NIH (R35 GM130387 to J.F.H. and F32-GM113404 to S.Y.L.). We thank the College of Chemistry’s NMR facility for resources provided and the staff for their assistance. Instruments in CoC-NMR are supported in part by the NIH (S10OD024998). A.T.A Thanks UC MEXUS-CONACYT for a Postdoctoral Research Fellowship. Publisher Copyright: ©

PY - 2021/2/5

Y1 - 2021/2/5

N2 - The direct, catalytic arylation of simple arenes in small excess with aryl bromides is disclosed. The developed method does not require the assistance of directing groups and relies on a synergistic catalytic cycle in which phosphine-ligated silver complexes cleave the aryl C-H bond, while palladium catalysts enable the formation of the biaryl products. Mechanistic experiments, including kinetic isotope effects, competition experiments, and hydrogen-deuterium exchange, support a catalytic cycle in which cleavage of the C-H bond by silver is the rate-determining step.

AB - The direct, catalytic arylation of simple arenes in small excess with aryl bromides is disclosed. The developed method does not require the assistance of directing groups and relies on a synergistic catalytic cycle in which phosphine-ligated silver complexes cleave the aryl C-H bond, while palladium catalysts enable the formation of the biaryl products. Mechanistic experiments, including kinetic isotope effects, competition experiments, and hydrogen-deuterium exchange, support a catalytic cycle in which cleavage of the C-H bond by silver is the rate-determining step.

UR - http://www.scopus.com/inward/record.url?scp=85099919634&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85099919634&partnerID=8YFLogxK

U2 - 10.1021/acscatal.0c05254

DO - 10.1021/acscatal.0c05254

M3 - Article

AN - SCOPUS:85099919634

SN - 2155-5435

VL - 11

SP - 1430

EP - 1434

JO - ACS Catalysis

JF - ACS Catalysis

IS - 3

ER -

Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this