Alkynes as Linchpins for the Additive Annulation of Biphenyls: Convergent Construction of Functionalized Fused Helicenes

A new approach to fused helicenes is reported, where varied substituents are readily incorporated in the extended aromatic frame. From the alkynyl precursor, the final helical compounds are obtained under mild conditions in a two‐step process, in which the final C−C bond is formed via a photochemica...

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Published inAngewandte Chemie International Edition Vol. 55; no. 39; pp. 12054 - 12058
Main Authors Mohamed, Rana K., Mondal, Sayantan, Guerrera, Joseph V., Eaton, Teresa M., Albrecht-Schmitt, Thomas E., Shatruk, Michael, Alabugin, Igor V.
Format Journal Article
LanguageEnglish
Published WEINHEIM Blackwell Publishing Ltd 19.09.2016
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkynes
Aromatic compounds
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Computer applications
helicenes
Photochemicals
photocyclodehydroiodination
Physical Sciences
Science & Technology
ACETYLENES
alkynes
PHOTOCHEMICAL-SYNTHESIS
photocyclodehydroiodination
EQUIVALENTS
ENYNE CYCLIZATIONS
RADICAL CASCADES
PHENANTHRENES
helicenes
COUPLING REACTION
TRIPHENYLENE
PHOTOCYCLIZATION
CARBOHELICENES
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Abstract A new approach to fused helicenes is reported, where varied substituents are readily incorporated in the extended aromatic frame. From the alkynyl precursor, the final helical compounds are obtained under mild conditions in a two‐step process, in which the final C−C bond is formed via a photochemical cyclization/ dehydroiodination sequence. The distortion of the π‐system from planarity leads to unusual packing in the solid state. Computational analysis reveals that substituent incorporation perturbs geometries and electronic structures of these nonplanar aromatics. A new approach to fused helicenes is reported, in which varied substituents are readily incorporated in the extended aromatic frame. From an alkynyl precursor, the final helical compounds are obtained in a two‐step process, in which the final C−C bond is photochemically forged by coupling cyclization and dehydroiodination. The distortion of the π‐system from planarity leads to unusual packing in the solid state.
AbstractList A new approach to fused helicenes is reported, where varied substituents are readily incorporated in the extended aromatic frame. From the alkynyl precursor, the final helical compounds are obtained under mild conditions in a two-step process, in which the final C-C bond is formed via a photochemical cyclization/ dehydroiodination sequence. The distortion of the π-system from planarity leads to unusual packing in the solid state. Computational analysis reveals that substituent incorporation perturbs geometries and electronic structures of these nonplanar aromatics.
A new approach to fused helicenes is reported, where varied substituents are readily incorporated in the extended aromatic frame. From the alkynyl precursor, the final helical compounds are obtained under mild conditions in a two-step process, in which the final C-C bond is formed via a photochemical cyclization/dehydroiodination sequence. The distortion of the p-system from planarity leads to unusual packing in the solid state. Computational analysis reveals that substituent incorporation perturbs geometries and electronic structures of these nonplanar aromatics.
A new approach to fused helicenes is reported, where varied substituents are readily incorporated in the extended aromatic frame. From the alkynyl precursor, the final helical compounds are obtained under mild conditions in a two‐step process, in which the final C−C bond is formed via a photochemical cyclization/ dehydroiodination sequence. The distortion of the π‐system from planarity leads to unusual packing in the solid state. Computational analysis reveals that substituent incorporation perturbs geometries and electronic structures of these nonplanar aromatics.
A new approach to fused helicenes is reported, where varied substituents are readily incorporated in the extended aromatic frame. From the alkynyl precursor, the final helical compounds are obtained under mild conditions in a two‐step process, in which the final C−C bond is formed via a photochemical cyclization/ dehydroiodination sequence. The distortion of the π‐system from planarity leads to unusual packing in the solid state. Computational analysis reveals that substituent incorporation perturbs geometries and electronic structures of these nonplanar aromatics. A new approach to fused helicenes is reported, in which varied substituents are readily incorporated in the extended aromatic frame. From an alkynyl precursor, the final helical compounds are obtained in a two‐step process, in which the final C−C bond is photochemically forged by coupling cyclization and dehydroiodination. The distortion of the π‐system from planarity leads to unusual packing in the solid state.
Author Shatruk, Michael
Alabugin, Igor V.
Albrecht-Schmitt, Thomas E.
Mohamed, Rana K.
Guerrera, Joseph V.
Eaton, Teresa M.
Mondal, Sayantan
Author_xml – sequence: 1
  givenname: Rana K.
  surname: Mohamed
  fullname: Mohamed, Rana K.
  organization: Department of Chemistry and Biochemistry, Florida State University, FL, 32310, Tallahassee, USA
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  givenname: Sayantan
  surname: Mondal
  fullname: Mondal, Sayantan
  organization: Department of Chemistry and Biochemistry, Florida State University, FL, 32310, Tallahassee, USA
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  givenname: Joseph V.
  surname: Guerrera
  fullname: Guerrera, Joseph V.
  organization: Department of Chemistry and Biochemistry, Florida State University, FL, 32310, Tallahassee, USA
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  givenname: Teresa M.
  surname: Eaton
  fullname: Eaton, Teresa M.
  organization: Department of Chemistry and Biochemistry, Florida State University, FL, 32310, Tallahassee, USA
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  givenname: Thomas E.
  surname: Albrecht-Schmitt
  fullname: Albrecht-Schmitt, Thomas E.
  organization: Department of Chemistry and Biochemistry, Florida State University, FL, 32310, Tallahassee, USA
– sequence: 6
  givenname: Michael
  surname: Shatruk
  fullname: Shatruk, Michael
  organization: Department of Chemistry and Biochemistry, Florida State University, FL, 32310, Tallahassee, USA
– sequence: 7
  givenname: Igor V.
  surname: Alabugin
  fullname: Alabugin, Igor V.
  email: alabugin@chem.fsu.edu
  organization: Department of Chemistry and Biochemistry, Florida State University, FL, 32310, Tallahassee, USA
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Issue 39
Keywords ACETYLENES
alkynes
PHOTOCHEMICAL-SYNTHESIS
photocyclodehydroiodination
EQUIVALENTS
ENYNE CYCLIZATIONS
RADICAL CASCADES
PHENANTHRENES
helicenes
COUPLING REACTION
TRIPHENYLENE
PHOTOCYCLIZATION
CARBOHELICENES
Language English
License http://onlinelibrary.wiley.com/termsAndConditions#am
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1984; 125
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1964; 86
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2007; 72
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2014; 2
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2012 2012; 51 124
2002; 43
2014; 16
2005 2005; 44 117
2008; 64
1985; 50
1903; 36
1971; 4
1965; 30
2001; 123
2015; 6
2013; 42
1967; 40
2008; 10
2003 2003; 42 115
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1992 1992; 31 104
2006 2006; 45 118
1984; 30
2016 2016; 55 128
2012; 112
1978; 43
2007; 111
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2015; 21
1973; 29
1969; 25
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2014; 79
2015; 119
1950; 166
1983; 48
1993; 115
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Tan Y.-Z. (e_1_2_2_5_1) 2013; 4
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Mallory F. B. (e_1_2_2_51_2) 1984; 30
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Snippet A new approach to fused helicenes is reported, where varied substituents are readily incorporated in the extended aromatic frame. From the alkynyl precursor,...
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StartPage 12054
SubjectTerms Alkynes
Aromatic compounds
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Computer applications
helicenes
Photochemicals
photocyclodehydroiodination
Physical Sciences
Science & Technology
Title Alkynes as Linchpins for the Additive Annulation of Biphenyls: Convergent Construction of Functionalized Fused Helicenes
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