Design and synthesis of new fluorinated ligands for the rhodium-catalyzed hydroformylation of alkenes in supercritical CO2 and fluorous solvents

Dominique Bonafoux; Zihao Hua; Beihan Wang; Iwao Ojima

doi:10.1016/S0022-1139(01)00473-0

Design and synthesis of new fluorinated ligands for the rhodium-catalyzed hydroformylation of alkenes in supercritical CO₂ and fluorous solvents

Dominique Bonafoux
, Zihao Hua
, Beihan Wang
, Iwao Ojima

Chemistry

Stony Brook University

Stony Brook University

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

54 Scopus citations

Abstract

Novel fluorous biphenols, 5,5′-[n-C₄F₉(CH₂)₃] ₂-2,2′-biphenol and 5,5′-[n-C₄F₉(CH₂)₃O] ₂-3,3′-di-tert-butyl-2,2′-biphenol, as well as enantiopure BINOLs, (S)-6,6′-[n-C₄F₉(CH₂)₃] ₂-BINOL, (R)-6,6′-[n-C₆F₁₃(CH₂)₃] ₂-BINOL, and (S)-6,6′-[n-C₈F₁₇(CH₂)₃] ₂-BINOL, are synthesized. These compounds serve as key intermediates for the syntheses of a variety of new fluorous ligands for regioselective and enantioselective catalytic reactions. Novel fluorous [Rf(CH₂)₃]₂-BINAPHOS ligands (Rf = n-C₄F₉, n-C₆F₁₃, and n-C₈F₁₇) are successfully synthesized. These new fluorous chiral ligands when used with a rhodium catalyst can achieve comparable or even higher regioselectivity and enantioselectivity in the asymmetric hydroformylation of styrene as compared to those by the Rh-BINAPHOS system.

Original language	English
Pages (from-to)	101-108
Number of pages	8
Journal	Journal of Fluorine Chemistry
Volume	112
Issue number	1
DOIs	https://doi.org/10.1016/S0022-1139(01)00473-0
State	Published - 2001

Keywords

Catalytic asymmetric synthesis
Diphosphite
Enantioselective
Fluorous BINAPHOS
Fluorous BINOL
Fluorous biphenol
Fluorous ligands
Hydroformylation
Phosphine-phosphite

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10.1016/S0022-1139(01)00473-0

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title = "Design and synthesis of new fluorinated ligands for the rhodium-catalyzed hydroformylation of alkenes in supercritical CO2 and fluorous solvents",

abstract = "Novel fluorous biphenols, 5,5′-[n-C4F9(CH2)3] 2-2,2′-biphenol and 5,5′-[n-C4F9(CH2)3O] 2-3,3′-di-tert-butyl-2,2′-biphenol, as well as enantiopure BINOLs, (S)-6,6′-[n-C4F9(CH2)3] 2-BINOL, (R)-6,6′-[n-C6F13(CH2)3] 2-BINOL, and (S)-6,6′-[n-C8F17(CH2)3] 2-BINOL, are synthesized. These compounds serve as key intermediates for the syntheses of a variety of new fluorous ligands for regioselective and enantioselective catalytic reactions. Novel fluorous [Rf(CH2)3]2-BINAPHOS ligands (Rf = n-C4F9, n-C6F13, and n-C8F17) are successfully synthesized. These new fluorous chiral ligands when used with a rhodium catalyst can achieve comparable or even higher regioselectivity and enantioselectivity in the asymmetric hydroformylation of styrene as compared to those by the Rh-BINAPHOS system.",

keywords = "Catalytic asymmetric synthesis, Diphosphite, Enantioselective, Fluorous BINAPHOS, Fluorous BINOL, Fluorous biphenol, Fluorous ligands, Hydroformylation, Phosphine-phosphite",

author = "Dominique Bonafoux and Zihao Hua and Beihan Wang and Iwao Ojima",

year = "2001",

doi = "10.1016/S0022-1139(01)00473-0",

language = "English",

volume = "112",

pages = "101--108",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

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T1 - Design and synthesis of new fluorinated ligands for the rhodium-catalyzed hydroformylation of alkenes in supercritical CO2 and fluorous solvents

AU - Bonafoux, Dominique

AU - Hua, Zihao

AU - Wang, Beihan

AU - Ojima, Iwao

PY - 2001

Y1 - 2001

N2 - Novel fluorous biphenols, 5,5′-[n-C4F9(CH2)3] 2-2,2′-biphenol and 5,5′-[n-C4F9(CH2)3O] 2-3,3′-di-tert-butyl-2,2′-biphenol, as well as enantiopure BINOLs, (S)-6,6′-[n-C4F9(CH2)3] 2-BINOL, (R)-6,6′-[n-C6F13(CH2)3] 2-BINOL, and (S)-6,6′-[n-C8F17(CH2)3] 2-BINOL, are synthesized. These compounds serve as key intermediates for the syntheses of a variety of new fluorous ligands for regioselective and enantioselective catalytic reactions. Novel fluorous [Rf(CH2)3]2-BINAPHOS ligands (Rf = n-C4F9, n-C6F13, and n-C8F17) are successfully synthesized. These new fluorous chiral ligands when used with a rhodium catalyst can achieve comparable or even higher regioselectivity and enantioselectivity in the asymmetric hydroformylation of styrene as compared to those by the Rh-BINAPHOS system.

AB - Novel fluorous biphenols, 5,5′-[n-C4F9(CH2)3] 2-2,2′-biphenol and 5,5′-[n-C4F9(CH2)3O] 2-3,3′-di-tert-butyl-2,2′-biphenol, as well as enantiopure BINOLs, (S)-6,6′-[n-C4F9(CH2)3] 2-BINOL, (R)-6,6′-[n-C6F13(CH2)3] 2-BINOL, and (S)-6,6′-[n-C8F17(CH2)3] 2-BINOL, are synthesized. These compounds serve as key intermediates for the syntheses of a variety of new fluorous ligands for regioselective and enantioselective catalytic reactions. Novel fluorous [Rf(CH2)3]2-BINAPHOS ligands (Rf = n-C4F9, n-C6F13, and n-C8F17) are successfully synthesized. These new fluorous chiral ligands when used with a rhodium catalyst can achieve comparable or even higher regioselectivity and enantioselectivity in the asymmetric hydroformylation of styrene as compared to those by the Rh-BINAPHOS system.

KW - Catalytic asymmetric synthesis

KW - Diphosphite

KW - Enantioselective

KW - Fluorous BINAPHOS

KW - Fluorous BINOL

KW - Fluorous biphenol

KW - Fluorous ligands

KW - Hydroformylation

KW - Phosphine-phosphite

UR - https://www.scopus.com/pages/publications/0035174901

U2 - 10.1016/S0022-1139(01)00473-0

DO - 10.1016/S0022-1139(01)00473-0

M3 - Article

SN - 0022-1139

VL - 112

SP - 101

EP - 108

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

IS - 1

ER -

Design and synthesis of new fluorinated ligands for the rhodium-catalyzed hydroformylation of alkenes in supercritical CO₂ and fluorous solvents

Abstract

Keywords

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