Understanding Polyarene Trifluoromethylation with Hot CF3 Radicals Using Corannulene

Igor V. Kuvychko; Tyler Clikeman; Cristina Dubceac; Yu Sheng Chen; Marina A. Petrukhina; Steven H. Strauss; Alexey A. Popov; Olga V. Boltalina

doi:10.1002/ejoc.201800508

Understanding Polyarene Trifluoromethylation with Hot CF₃ Radicals Using Corannulene

Igor V. Kuvychko
, Tyler Clikeman
, Cristina Dubceac
, Yu Sheng Chen
, Marina A. Petrukhina
, Steven H. Strauss
, Alexey A. Popov
, Olga V. Boltalina

Chemistry

University at Albany

Colorado State University
SUNY Albany
United States Department of Energy
Leibniz Institute for Solid State and Materials Research Dresden

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

11 Scopus citations

Abstract

New insights into the process of high-temperature trifluoromethylation of polycyclic aromatic hydrocarbons (PAHs) were gained in a detailed study of the reactions between corannulene (C₂₀H₁₀) and CF₃I gas. Ten new poly(trifluoromethyl)corannulenes were made in these reactions and were fully characterized. A detailed computational study explains the observed trends in the product distribution and why some products cannot be prepared even with an excess of the reagent gas. The approach utilized here may have good predictive value for designing new effective and selective synthetic methodologies for various thermally stable electron-deficient PAHs.

Original language	English
Pages (from-to)	4233-4245
Number of pages	13
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	31
DOIs	https://doi.org/10.1002/ejoc.201800508
State	Published - Aug 23 2018

Keywords

Corannulene
DFT calculations
Fluorinated compounds
Molecular structure
Trifluoromethylation

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10.1002/ejoc.201800508

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title = "Understanding Polyarene Trifluoromethylation with Hot CF3 Radicals Using Corannulene",

abstract = "New insights into the process of high-temperature trifluoromethylation of polycyclic aromatic hydrocarbons (PAHs) were gained in a detailed study of the reactions between corannulene (C20H10) and CF3I gas. Ten new poly(trifluoromethyl)corannulenes were made in these reactions and were fully characterized. A detailed computational study explains the observed trends in the product distribution and why some products cannot be prepared even with an excess of the reagent gas. The approach utilized here may have good predictive value for designing new effective and selective synthetic methodologies for various thermally stable electron-deficient PAHs.",

keywords = "Corannulene, DFT calculations, Fluorinated compounds, Molecular structure, Trifluoromethylation",

author = "Kuvychko, \{Igor V.\} and Tyler Clikeman and Cristina Dubceac and Chen, \{Yu Sheng\} and Petrukhina, \{Marina A.\} and Strauss, \{Steven H.\} and Popov, \{Alexey A.\} and Boltalina, \{Olga V.\}",

note = "Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = aug,

day = "23",

doi = "10.1002/ejoc.201800508",

language = "English",

volume = "2018",

pages = "4233--4245",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH Verlag",

number = "31",

}

TY - JOUR

T1 - Understanding Polyarene Trifluoromethylation with Hot CF3 Radicals Using Corannulene

AU - Kuvychko, Igor V.

AU - Clikeman, Tyler

AU - Dubceac, Cristina

AU - Chen, Yu Sheng

AU - Petrukhina, Marina A.

AU - Strauss, Steven H.

AU - Popov, Alexey A.

AU - Boltalina, Olga V.

PY - 2018/8/23

Y1 - 2018/8/23

N2 - New insights into the process of high-temperature trifluoromethylation of polycyclic aromatic hydrocarbons (PAHs) were gained in a detailed study of the reactions between corannulene (C20H10) and CF3I gas. Ten new poly(trifluoromethyl)corannulenes were made in these reactions and were fully characterized. A detailed computational study explains the observed trends in the product distribution and why some products cannot be prepared even with an excess of the reagent gas. The approach utilized here may have good predictive value for designing new effective and selective synthetic methodologies for various thermally stable electron-deficient PAHs.

AB - New insights into the process of high-temperature trifluoromethylation of polycyclic aromatic hydrocarbons (PAHs) were gained in a detailed study of the reactions between corannulene (C20H10) and CF3I gas. Ten new poly(trifluoromethyl)corannulenes were made in these reactions and were fully characterized. A detailed computational study explains the observed trends in the product distribution and why some products cannot be prepared even with an excess of the reagent gas. The approach utilized here may have good predictive value for designing new effective and selective synthetic methodologies for various thermally stable electron-deficient PAHs.

KW - Corannulene

KW - DFT calculations

KW - Fluorinated compounds

KW - Molecular structure

KW - Trifluoromethylation

UR - https://www.scopus.com/pages/publications/85050757148

U2 - 10.1002/ejoc.201800508

DO - 10.1002/ejoc.201800508

M3 - Article

SN - 1434-193X

VL - 2018

SP - 4233

EP - 4245

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 31

ER -

Understanding Polyarene Trifluoromethylation with Hot CF₃ Radicals Using Corannulene

Abstract

Keywords

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