Rhodium-Catalyzed Atroposelective C–H Arylation: Efficient Synthesis of Axially Chiral Heterobiaryls

Rhodium­(I)-catalyzed atroposelective C–H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh­(C2H4)2Cl]2 and a TADDOL-derived monodentate phosphonite, with 2-pyridine, 2-isoquinoline and their analogs as directing groups, a series of axially chiral heterobiar...

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Published inJournal of the American Chemical Society Vol. 141; no. 24; pp. 9504 - 9510
Main Authors Wang, Qiang, Cai, Zhong-Jian, Liu, Chen-Xu, Gu, Qing, You, Shu-Li
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.06.2019
Amer Chemical Soc
Subjects
alcohols
allylation
arylation
benzaldehyde
carbon-hydrogen bond activation
catalysts
catalytic activity
Chemistry
Chemistry, Multidisciplinary
enantioselectivity
ethylene
ligands
nitrogen oxides
Physical Sciences
rhodium
Science & Technology
BRONSTED ACID
FUNCTIONALIZATION
ACTIVATION
BIARYL ATROPISOMERS
OLEFINATION
ENANTIOSELECTIVE SYNTHESIS
LIGANDS
NATURAL-PRODUCTS
PROGRESS
ALDEHYDES
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Abstract Rhodium­(I)-catalyzed atroposelective C–H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh­(C2H4)2Cl]2 and a TADDOL-derived monodentate phosphonite, with 2-pyridine, 2-isoquinoline and their analogs as directing groups, a series of axially chiral heterobiaryls were obtained in excellent yields and enantioselectivities (up to 99% yield, 97% ee) via C–H direct functionalization reaction. The products obtained from this method provide a platform for the synthesis of axially chiral biaryl ligands and catalysts. As a demonstration, a chiral N-oxide synthesized from the product in one step could act as an efficient catalyst for asymmetric allylation of benzaldehyde with allyltrichlorosilane, leading to homoallyl alcohol with excellent enantiocontrol.
AbstractList Rhodium­(I)-catalyzed atroposelective C–H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh­(C2H4)2Cl]2 and a TADDOL-derived monodentate phosphonite, with 2-pyridine, 2-isoquinoline and their analogs as directing groups, a series of axially chiral heterobiaryls were obtained in excellent yields and enantioselectivities (up to 99% yield, 97% ee) via C–H direct functionalization reaction. The products obtained from this method provide a platform for the synthesis of axially chiral biaryl ligands and catalysts. As a demonstration, a chiral N-oxide synthesized from the product in one step could act as an efficient catalyst for asymmetric allylation of benzaldehyde with allyltrichlorosilane, leading to homoallyl alcohol with excellent enantiocontrol.
Rhodium(I)-catalyzed atroposelective C-H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C2H4)(2) CH2 and a TADDOL-derived monodentate phosphonite, with 2-pyridine, 2-isoquinoline and their analogs as directing groups, a series of axially chiral heterobiaryls were obtained in excellent yields and enantioselectivities (up to 99% yield, 97% ee) via C-H direct functionalization reaction. The products obtained from this method provide a platform for the synthesis of axially chiral biaryl ligands and catalysts. As a demonstration, a chiral N-oxide synthesized from the product in one step could act as an efficient catalyst for asymmetric allylation of benzaldehyde with allyltrichlorosilane, leading to homoallyl alcohol with excellent enantiocontrol.
Rhodium(I)-catalyzed atroposelective C–H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C₂H₄)₂Cl]₂ and a TADDOL-derived monodentate phosphonite, with 2-pyridine, 2-isoquinoline and their analogs as directing groups, a series of axially chiral heterobiaryls were obtained in excellent yields and enantioselectivities (up to 99% yield, 97% ee) via C–H direct functionalization reaction. The products obtained from this method provide a platform for the synthesis of axially chiral biaryl ligands and catalysts. As a demonstration, a chiral N-oxide synthesized from the product in one step could act as an efficient catalyst for asymmetric allylation of benzaldehyde with allyltrichlorosilane, leading to homoallyl alcohol with excellent enantiocontrol.
Rhodium(I)-catalyzed atroposelective C-H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C2H4)2Cl]2 and a TADDOL-derived monodentate phosphonite, with 2-pyridine, 2-isoquinoline and their analogs as directing groups, a series of axially chiral heterobiaryls were obtained in excellent yields and enantioselectivities (up to 99% yield, 97% ee) via C-H direct functionalization reaction. The products obtained from this method provide a platform for the synthesis of axially chiral biaryl ligands and catalysts. As a demonstration, a chiral N-oxide synthesized from the product in one step could act as an efficient catalyst for asymmetric allylation of benzaldehyde with allyltrichlorosilane, leading to homoallyl alcohol with excellent enantiocontrol.Rhodium(I)-catalyzed atroposelective C-H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C2H4)2Cl]2 and a TADDOL-derived monodentate phosphonite, with 2-pyridine, 2-isoquinoline and their analogs as directing groups, a series of axially chiral heterobiaryls were obtained in excellent yields and enantioselectivities (up to 99% yield, 97% ee) via C-H direct functionalization reaction. The products obtained from this method provide a platform for the synthesis of axially chiral biaryl ligands and catalysts. As a demonstration, a chiral N-oxide synthesized from the product in one step could act as an efficient catalyst for asymmetric allylation of benzaldehyde with allyltrichlorosilane, leading to homoallyl alcohol with excellent enantiocontrol.
Rhodium(I)-catalyzed atroposelective C-H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C H ) Cl] and a TADDOL-derived monodentate phosphonite, with 2-pyridine, 2-isoquinoline and their analogs as directing groups, a series of axially chiral heterobiaryls were obtained in excellent yields and enantioselectivities (up to 99% yield, 97% ee) via C-H direct functionalization reaction. The products obtained from this method provide a platform for the synthesis of axially chiral biaryl ligands and catalysts. As a demonstration, a chiral N-oxide synthesized from the product in one step could act as an efficient catalyst for asymmetric allylation of benzaldehyde with allyltrichlorosilane, leading to homoallyl alcohol with excellent enantiocontrol.
Author You, Shu-Li
Gu, Qing
Wang, Qiang
Cai, Zhong-Jian
Liu, Chen-Xu
Author_xml – sequence: 1
  givenname: Qiang
  surname: Wang
  fullname: Wang, Qiang
– sequence: 2
  givenname: Zhong-Jian
  surname: Cai
  fullname: Cai, Zhong-Jian
– sequence: 3
  givenname: Chen-Xu
  surname: Liu
  fullname: Liu, Chen-Xu
– sequence: 4
  givenname: Qing
  orcidid: 0000-0003-4963-2271
  surname: Gu
  fullname: Gu, Qing
– sequence: 5
  givenname: Shu-Li
  orcidid: 0000-0003-4586-8359
  surname: You
  fullname: You, Shu-Li
  email: slyou@sioc.ac.cn
BackLink https://www.ncbi.nlm.nih.gov/pubmed/31184139$$D View this record in MEDLINE/PubMed
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Issue 24
Keywords BRONSTED ACID
FUNCTIONALIZATION
ACTIVATION
BIARYL ATROPISOMERS
OLEFINATION
ENANTIOSELECTIVE SYNTHESIS
LIGANDS
NATURAL-PRODUCTS
PROGRESS
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Snippet Rhodium­(I)-catalyzed atroposelective C–H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh­(C2H4)2Cl]2 and a...
Rhodium(I)-catalyzed atroposelective C-H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C2H4)(2) CH2 and a...
Rhodium(I)-catalyzed atroposelective C-H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C H ) Cl] and a...
Rhodium(I)-catalyzed atroposelective C-H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C2H4)2Cl]2 and a...
Rhodium(I)-catalyzed atroposelective C–H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C₂H₄)₂Cl]₂ and a...
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SubjectTerms alcohols
allylation
arylation
benzaldehyde
carbon-hydrogen bond activation
catalysts
catalytic activity
Chemistry
Chemistry, Multidisciplinary
enantioselectivity
ethylene
ligands
nitrogen oxides
Physical Sciences
rhodium
Science & Technology
Title Rhodium-Catalyzed Atroposelective C–H Arylation: Efficient Synthesis of Axially Chiral Heterobiaryls
URI http://dx.doi.org/10.1021/jacs.9b03862
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https://www.ncbi.nlm.nih.gov/pubmed/31184139
https://www.proquest.com/docview/2242153862
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