Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands

Hari P.R. Mangunuru; Christian A. Malapit; Nizar Haddad; Jonathan T. Reeves; Bo Qu; Sonia Rodriguez; Heewon Lee; Nathan K. Yee; Jinhua J. Song; Carl A. Busacca; Chris H. Senanayake

doi:10.1055/s-0036-1591590

Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands

Hari P.R. Mangunuru, Christian A. Malapit, Nizar Haddad^*, Jonathan T. Reeves, Bo Qu, Sonia Rodriguez, Heewon Lee, Nathan K. Yee, Jinhua J. Song, Carl A. Busacca, Chris H. Senanayake

^*Corresponding author for this work

Chemistry

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

4 Scopus citations

Abstract

The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i -Pr-BI-DIME and Me ₂ -BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd ₂ (dba) ₃ / i -Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me ₂ -BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.

Original language	English (US)
Pages (from-to)	4435-4443
Number of pages	9
Journal	Synthesis (Germany)
Volume	50
Issue number	22
DOIs	https://doi.org/10.1055/s-0036-1591590
State	Published - 2018

Keywords

BI-DIME
Pd catalysis
arylation
asymmetric
oxindoles

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0036-1591590

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title = "Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands",

abstract = "The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i -Pr-BI-DIME and Me 2 -BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd 2 (dba) 3 / i -Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me 2 -BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.",

keywords = "BI-DIME, Pd catalysis, arylation, asymmetric, oxindoles",

author = "Mangunuru, {Hari P.R.} and Malapit, {Christian A.} and Nizar Haddad and Reeves, {Jonathan T.} and Bo Qu and Sonia Rodriguez and Heewon Lee and Yee, {Nathan K.} and Song, {Jinhua J.} and Busacca, {Carl A.} and Senanayake, {Chris H.}",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart - New York.",

year = "2018",

doi = "10.1055/s-0036-1591590",

language = "English (US)",

volume = "50",

pages = "4435--4443",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "22",

}

TY - JOUR

T1 - Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands

AU - Mangunuru, Hari P.R.

AU - Malapit, Christian A.

AU - Haddad, Nizar

AU - Reeves, Jonathan T.

AU - Qu, Bo

AU - Rodriguez, Sonia

AU - Lee, Heewon

AU - Yee, Nathan K.

AU - Song, Jinhua J.

AU - Busacca, Carl A.

AU - Senanayake, Chris H.

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart - New York.

PY - 2018

Y1 - 2018

N2 - The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i -Pr-BI-DIME and Me 2 -BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd 2 (dba) 3 / i -Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me 2 -BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.

AB - The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i -Pr-BI-DIME and Me 2 -BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd 2 (dba) 3 / i -Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me 2 -BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.

KW - BI-DIME

KW - Pd catalysis

KW - arylation

KW - asymmetric

KW - oxindoles

UR - http://www.scopus.com/inward/record.url?scp=85056079083&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85056079083&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1591590

DO - 10.1055/s-0036-1591590

M3 - Article

AN - SCOPUS:85056079083

SN - 0039-7881

VL - 50

SP - 4435

EP - 4443

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 22

ER -

Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands

Abstract

Keywords

ASJC Scopus subject areas

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