A Resorcin[4]arene-Based Phosphite-Phosphine Ligand for the Branched-Selective Hydroformylation of Alkyl Alkenes

Jennifer E. Smart; Jack Emerson-King; Rebekah J. Jeans; Thomas M. Hood; Samantha Lau; Alejandro Bara-Estaún; Ulrich Hintermair; Paul G. Pringle; Adrian B. Chaplin

doi:10.1021/acscatal.4c03510

A Resorcin[4]arene-Based Phosphite-Phosphine Ligand for the Branched-Selective Hydroformylation of Alkyl Alkenes

Jennifer E. Smart
, Jack Emerson-King
, Rebekah J. Jeans
, Thomas M. Hood
, Samantha Lau
, Alejandro Bara-Estaún
, Ulrich Hintermair
, Paul G. Pringle
, Adrian B. Chaplin

University of Warwick
University of Bristol
Dynamic Reaction Monitoring Facility

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

14 Citations (SciVal)

Abstract

Synthesis of a chelating phosphite-phosphine ligand from a tris(quinoxaline) extended resorcin[4]arene and its application in the rhodium-catalyzed hydroformylation of terminal alkyl alkenes are reported. Rhodium complexes are formed within the cavity of the macrocycle and branched-selective hydroformylation of 1-octene with a b/l ratio of 5.9 has been achieved at 60 °C under 1:1 H₂/CO (20 bar).

Original language	English
Pages (from-to)	11803-11807
Number of pages	5
Journal	ACS Catalysis
Volume	14
Issue number	15
Early online date	24 Jul 2024
DOIs	https://doi.org/10.1021/acscatal.4c03510
Publication status	Published - 2 Aug 2024

Funding

We gratefully acknowledge funding from the Royal Society (RGF\\EA\\180128, J.E.S.; UF160458, URF\\R\\221049, U.H.; UF100592, UF150675; A.B.C.), EPSRC (DTA studentship to J.E.-K.; EP/R027129/1, R.J.J.; EP/L016443, A.B.-E.), Leverhulme Trust (RPG-2022-214, T.M.H.), and European Research Council (ERC; grant agreement 637313, S.L., A.B.C.). We thank Dr. Catherine Lyall, Dr. John Lowe and the Chemical Characterisation Facility (MC) at the University of Bath ( 10.15125/mx6j-3r54 ) for technical support in collecting NMR data using the EPSRC-funded Dynamic Reaction Monitoring Facility (EP/P001475/1). Crystallographic data were collected using an instrument that received funding from the ERC under the European Union\u2019s Horizon 2020 research and innovation programme (grant agreement No. 637313).

Funders	Funder number
EU - Horizon 2020
Royal Society	URF\R\221049, UF160458, RGF\EA\180128, UF100592, UF150675
EPSRC Centre for Doctoral Training in Cyber Security	EP/L016443, EP/R027129/1
The Leverhulme Trust	RPG-2022-214
European Research Council	637313

Keywords

cavitand ligands
chelating phosphine ligands
hydroformylation
regioselectivity
rhodium catalysts

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1021/acscatal.4c03510Licence: CC BY

Cite this

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title = "A Resorcin[4]arene-Based Phosphite-Phosphine Ligand for the Branched-Selective Hydroformylation of Alkyl Alkenes",

abstract = "Synthesis of a chelating phosphite-phosphine ligand from a tris(quinoxaline) extended resorcin[4]arene and its application in the rhodium-catalyzed hydroformylation of terminal alkyl alkenes are reported. Rhodium complexes are formed within the cavity of the macrocycle and branched-selective hydroformylation of 1-octene with a b/l ratio of 5.9 has been achieved at 60 °C under 1:1 H2/CO (20 bar).",

keywords = "cavitand ligands, chelating phosphine ligands, hydroformylation, regioselectivity, rhodium catalysts",

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doi = "10.1021/acscatal.4c03510",

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journal = "ACS Catalysis",

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TY - JOUR

T1 - A Resorcin[4]arene-Based Phosphite-Phosphine Ligand for the Branched-Selective Hydroformylation of Alkyl Alkenes

AU - Smart, Jennifer E.

AU - Emerson-King, Jack

AU - Jeans, Rebekah J.

AU - Hood, Thomas M.

AU - Lau, Samantha

AU - Bara-Estaún, Alejandro

AU - Hintermair, Ulrich

AU - Pringle, Paul G.

AU - Chaplin, Adrian B.

PY - 2024/8/2

Y1 - 2024/8/2

N2 - Synthesis of a chelating phosphite-phosphine ligand from a tris(quinoxaline) extended resorcin[4]arene and its application in the rhodium-catalyzed hydroformylation of terminal alkyl alkenes are reported. Rhodium complexes are formed within the cavity of the macrocycle and branched-selective hydroformylation of 1-octene with a b/l ratio of 5.9 has been achieved at 60 °C under 1:1 H2/CO (20 bar).

AB - Synthesis of a chelating phosphite-phosphine ligand from a tris(quinoxaline) extended resorcin[4]arene and its application in the rhodium-catalyzed hydroformylation of terminal alkyl alkenes are reported. Rhodium complexes are formed within the cavity of the macrocycle and branched-selective hydroformylation of 1-octene with a b/l ratio of 5.9 has been achieved at 60 °C under 1:1 H2/CO (20 bar).

KW - cavitand ligands

KW - chelating phosphine ligands

KW - hydroformylation

KW - regioselectivity

KW - rhodium catalysts

UR - https://www.scopus.com/pages/publications/85199531449

U2 - 10.1021/acscatal.4c03510

DO - 10.1021/acscatal.4c03510

M3 - Letter

AN - SCOPUS:85199531449

SN - 2155-5435

VL - 14

SP - 11803

EP - 11807

JO - ACS Catalysis

JF - ACS Catalysis

IS - 15

ER -

A Resorcin[4]arene-Based Phosphite-Phosphine Ligand for the Branched-Selective Hydroformylation of Alkyl Alkenes

Abstract

Funding

Keywords

ASJC Scopus subject areas

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