Pd-Catalyzed C−H Alkylation of Arenes Using PyrDipSi, a Transformable and Removable Silicon-Tethered Directing Group

Dhruba Sarkar; Vladimir Gevorgyan

doi:10.1002/chem.201602513

Pd-Catalyzed C−H Alkylation of Arenes Using PyrDipSi, a Transformable and Removable Silicon-Tethered Directing Group

Dhruba Sarkar, Vladimir Gevorgyan

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

22 Scopus citations

Abstract

An efficient Pd-catalyzed ortho-C−H alkylation reaction of arenes using a transformable and removable Si-tethered pyridyldiisopropylsilyl (PyrDipSi) directing group has been developed. In addition, the PyrDipSi directing group allows for an efficient sequential double-fold C−H alkylation/oxygenation of arenes to produce meta-alkylated phenols. This directing group can easily be removed or converted into valuable functionalities, such as aryl, iodo, boronic ester, or phenol.

Original language	English (US)
Pages (from-to)	11201-11204
Number of pages	4
Journal	Chemistry - A European Journal
Volume	22
Issue number	32
DOIs	https://doi.org/10.1002/chem.201602513
State	Published - Aug 1 2016
Externally published	Yes

Keywords

C−H alkylation
catalysis
directing group
palladium
silicon

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201602513

Cite this

@article{6b7f3f03b2f6484aaf1a38e586304c95,

title = "Pd-Catalyzed C−H Alkylation of Arenes Using PyrDipSi, a Transformable and Removable Silicon-Tethered Directing Group",

abstract = "An efficient Pd-catalyzed ortho-C−H alkylation reaction of arenes using a transformable and removable Si-tethered pyridyldiisopropylsilyl (PyrDipSi) directing group has been developed. In addition, the PyrDipSi directing group allows for an efficient sequential double-fold C−H alkylation/oxygenation of arenes to produce meta-alkylated phenols. This directing group can easily be removed or converted into valuable functionalities, such as aryl, iodo, boronic ester, or phenol.",

keywords = "C−H alkylation, catalysis, directing group, palladium, silicon",

author = "Dhruba Sarkar and Vladimir Gevorgyan",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = aug,

day = "1",

doi = "10.1002/chem.201602513",

language = "English (US)",

volume = "22",

pages = "11201--11204",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "32",

}

TY - JOUR

T1 - Pd-Catalyzed C−H Alkylation of Arenes Using PyrDipSi, a Transformable and Removable Silicon-Tethered Directing Group

AU - Sarkar, Dhruba

AU - Gevorgyan, Vladimir

PY - 2016/8/1

Y1 - 2016/8/1

N2 - An efficient Pd-catalyzed ortho-C−H alkylation reaction of arenes using a transformable and removable Si-tethered pyridyldiisopropylsilyl (PyrDipSi) directing group has been developed. In addition, the PyrDipSi directing group allows for an efficient sequential double-fold C−H alkylation/oxygenation of arenes to produce meta-alkylated phenols. This directing group can easily be removed or converted into valuable functionalities, such as aryl, iodo, boronic ester, or phenol.

AB - An efficient Pd-catalyzed ortho-C−H alkylation reaction of arenes using a transformable and removable Si-tethered pyridyldiisopropylsilyl (PyrDipSi) directing group has been developed. In addition, the PyrDipSi directing group allows for an efficient sequential double-fold C−H alkylation/oxygenation of arenes to produce meta-alkylated phenols. This directing group can easily be removed or converted into valuable functionalities, such as aryl, iodo, boronic ester, or phenol.

KW - C−H alkylation

KW - catalysis

KW - directing group

KW - palladium

KW - silicon

UR - http://www.scopus.com/inward/record.url?scp=84979710839&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84979710839&partnerID=8YFLogxK

U2 - 10.1002/chem.201602513

DO - 10.1002/chem.201602513

M3 - Article

C2 - 27272930

AN - SCOPUS:84979710839

SN - 0947-6539

VL - 22

SP - 11201

EP - 11204

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 32

ER -

Pd-Catalyzed C−H Alkylation of Arenes Using PyrDipSi, a Transformable and Removable Silicon-Tethered Directing Group

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this