Application of P-Bridged Biaryl Phosphines in Pd-Catalyzed α-Arylation Reactions

Malibongwe P. Shandu; Jairus L. Lamola; Cedric W. Holzapfel; Munaka Christopher Maumela; Paseka T. Moshapo

doi:10.1002/slct.202203712

Application of P-Bridged Biaryl Phosphines in Pd-Catalyzed α-Arylation Reactions

Malibongwe P. Shandu, Jairus L. Lamola, Cedric W. Holzapfel, Munaka Christopher Maumela, Paseka T. Moshapo

Chemical Sciences

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

1 Citation (Scopus)

Abstract

The use of catalysts derived from Pd₂(dba)₃ and phosphatrioxa-adamantane framework (Cg) has been demonstrated to facilitate the effective alpha(α)-arylation of ketones using a diverse array of aryl halides under mild reaction conditions (40 °C–80 °C). The evaluation of phosphines with dissimilar stereoelectronic properties revealed the pivotal role of fine-tuning the ligand's steric bulk. In particular, catalysts based on the Cg-biphenyl ligand (1) proved efficient for facile α-arylation of electronically and sterically diverse aryl bromides and chlorides.

Original language	English
Article number	e202203712
Journal	ChemistrySelect
Volume	7
Issue number	41
DOIs	https://doi.org/10.1002/slct.202203712
Publication status	Published - 7 Nov 2022

Keywords

Biaryl phosphines •
Cross-coupling
Pd-catalysis
Phobane
Phosphatrioxa-adamantane
α-Arylation

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1002/slct.202203712

Cite this

@article{989e13aa408c4e069f082fd13b73bd71,

title = "Application of P-Bridged Biaryl Phosphines in Pd-Catalyzed α-Arylation Reactions",

abstract = "The use of catalysts derived from Pd2(dba)3 and phosphatrioxa-adamantane framework (Cg) has been demonstrated to facilitate the effective alpha(α)-arylation of ketones using a diverse array of aryl halides under mild reaction conditions (40 °C–80 °C). The evaluation of phosphines with dissimilar stereoelectronic properties revealed the pivotal role of fine-tuning the ligand's steric bulk. In particular, catalysts based on the Cg-biphenyl ligand (1) proved efficient for facile α-arylation of electronically and sterically diverse aryl bromides and chlorides.",

keywords = "Biaryl phosphines •, Cross-coupling, Pd-catalysis, Phobane, Phosphatrioxa-adamantane, α-Arylation",

author = "Shandu, {Malibongwe P.} and Lamola, {Jairus L.} and Holzapfel, {Cedric W.} and Maumela, {Munaka Christopher} and Moshapo, {Paseka T.}",

note = "Publisher Copyright: {\textcopyright} 2022 The Authors. ChemistrySelect published by Wiley-VCH GmbH.",

year = "2022",

month = nov,

day = "7",

doi = "10.1002/slct.202203712",

language = "English",

volume = "7",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley-Blackwell Publishing Ltd",

number = "41",

}

TY - JOUR

T1 - Application of P-Bridged Biaryl Phosphines in Pd-Catalyzed α-Arylation Reactions

AU - Shandu, Malibongwe P.

AU - Lamola, Jairus L.

AU - Holzapfel, Cedric W.

AU - Maumela, Munaka Christopher

AU - Moshapo, Paseka T.

PY - 2022/11/7

Y1 - 2022/11/7

N2 - The use of catalysts derived from Pd2(dba)3 and phosphatrioxa-adamantane framework (Cg) has been demonstrated to facilitate the effective alpha(α)-arylation of ketones using a diverse array of aryl halides under mild reaction conditions (40 °C–80 °C). The evaluation of phosphines with dissimilar stereoelectronic properties revealed the pivotal role of fine-tuning the ligand's steric bulk. In particular, catalysts based on the Cg-biphenyl ligand (1) proved efficient for facile α-arylation of electronically and sterically diverse aryl bromides and chlorides.

AB - The use of catalysts derived from Pd2(dba)3 and phosphatrioxa-adamantane framework (Cg) has been demonstrated to facilitate the effective alpha(α)-arylation of ketones using a diverse array of aryl halides under mild reaction conditions (40 °C–80 °C). The evaluation of phosphines with dissimilar stereoelectronic properties revealed the pivotal role of fine-tuning the ligand's steric bulk. In particular, catalysts based on the Cg-biphenyl ligand (1) proved efficient for facile α-arylation of electronically and sterically diverse aryl bromides and chlorides.

KW - Biaryl phosphines •

KW - Cross-coupling

KW - Pd-catalysis

KW - Phobane

KW - Phosphatrioxa-adamantane

KW - α-Arylation

UR - http://www.scopus.com/inward/record.url?scp=85141721449&partnerID=8YFLogxK

U2 - 10.1002/slct.202203712

DO - 10.1002/slct.202203712

M3 - Article

AN - SCOPUS:85141721449

SN - 2365-6549

VL - 7

JO - ChemistrySelect

JF - ChemistrySelect

IS - 41

M1 - e202203712

ER -

Application of P-Bridged Biaryl Phosphines in Pd-Catalyzed α-Arylation Reactions

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this