Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation

Bo Chen; Xue Long Hou; Yu Xue Li; Yun Dong Wu

doi:10.1021/ja201425e

Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation

Bo Chen, Xue Long Hou, Yu Xue Li, Yun Dong Wu

Chemistry

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

202 Scopus citations

Abstract

DFT calculations suggest that the unexpected meta product in the copper-catalyzed arylation of anilide is formed via a Heck-like four-membered-ring transition state involving a Cu^III-Ph species. A competitive electrophilic substitution mechanism delivers the ortho product when a methoxy group is present at the meta position of pivanilide. A series of experiments including kinetic studies support the involvement of a Cu ^I catalyst.

Original language	English (US)
Pages (from-to)	7668-7671
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	20
DOIs	https://doi.org/10.1021/ja201425e
State	Published - May 25 2011

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja201425e

Cite this

@article{15cd0bde9acc42e38d45132bb63c2451,

title = "Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation",

abstract = "DFT calculations suggest that the unexpected meta product in the copper-catalyzed arylation of anilide is formed via a Heck-like four-membered-ring transition state involving a CuIII-Ph species. A competitive electrophilic substitution mechanism delivers the ortho product when a methoxy group is present at the meta position of pivanilide. A series of experiments including kinetic studies support the involvement of a Cu I catalyst.",

author = "Bo Chen and Hou, {Xue Long} and Li, {Yu Xue} and Wu, {Yun Dong}",

year = "2011",

month = may,

day = "25",

doi = "10.1021/ja201425e",

language = "English (US)",

volume = "133",

pages = "7668--7671",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation

AU - Chen, Bo

AU - Hou, Xue Long

AU - Li, Yu Xue

AU - Wu, Yun Dong

PY - 2011/5/25

Y1 - 2011/5/25

N2 - DFT calculations suggest that the unexpected meta product in the copper-catalyzed arylation of anilide is formed via a Heck-like four-membered-ring transition state involving a CuIII-Ph species. A competitive electrophilic substitution mechanism delivers the ortho product when a methoxy group is present at the meta position of pivanilide. A series of experiments including kinetic studies support the involvement of a Cu I catalyst.

AB - DFT calculations suggest that the unexpected meta product in the copper-catalyzed arylation of anilide is formed via a Heck-like four-membered-ring transition state involving a CuIII-Ph species. A competitive electrophilic substitution mechanism delivers the ortho product when a methoxy group is present at the meta position of pivanilide. A series of experiments including kinetic studies support the involvement of a Cu I catalyst.

UR - http://www.scopus.com/inward/record.url?scp=79957678090&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79957678090&partnerID=8YFLogxK

U2 - 10.1021/ja201425e

DO - 10.1021/ja201425e

M3 - Article

C2 - 21520975

AN - SCOPUS:79957678090

SN - 0002-7863

VL - 133

SP - 7668

EP - 7671

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 20

ER -

Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this