Atom efficient synthesis of selectively difluorinated carbocycles through a gold(I) catalyzed cyclization

Adam W. McCarter, Magdalana Sommer, Jonathan M. Percy, Craig Jamieson, Alan R. Kennedy, David J. Hirst

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The intramolecular carbocyclization of difluorinated enol acetals has been achieved for the first time using gold(I) catalysis. Difluorinated enol acetals bearing a pendant alkene group can be cyclized and reduced in one pot to form fluorinated diol motifs. Alternatively, the cyclization of terminal alkynes allows for the synthesis of fluorinated pyran scaffolds. Both cyclization processes can be performed under mild conditions allowing access to complex products rich in functionality. The cyclic systems are synthesized concisely (maximum four steps) from trifluoroethanol, an inexpensive fluorinated feedstock.
LanguageEnglish
JournalJournal of Organic Chemistry
Early online date6 Jul 2018
DOIs
Publication statusE-pub ahead of print - 6 Jul 2018

Fingerprint

Acetals
Cyclization
Gold
Bearings (structural)
Trifluoroethanol
Pyrans
Atoms
Alkynes
Alkenes
Scaffolds
Feedstocks
Catalysis

Keywords

  • gold(I) catalysis
  • cyclization processes
  • synthesis

Cite this

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title = "Atom efficient synthesis of selectively difluorinated carbocycles through a gold(I) catalyzed cyclization",
abstract = "The intramolecular carbocyclization of difluorinated enol acetals has been achieved for the first time using gold(I) catalysis. Difluorinated enol acetals bearing a pendant alkene group can be cyclized and reduced in one pot to form fluorinated diol motifs. Alternatively, the cyclization of terminal alkynes allows for the synthesis of fluorinated pyran scaffolds. Both cyclization processes can be performed under mild conditions allowing access to complex products rich in functionality. The cyclic systems are synthesized concisely (maximum four steps) from trifluoroethanol, an inexpensive fluorinated feedstock.",
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author = "McCarter, {Adam W.} and Magdalana Sommer and Percy, {Jonathan M.} and Craig Jamieson and Kennedy, {Alan R.} and Hirst, {David J.}",
year = "2018",
month = "7",
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doi = "10.1021/acs.joc.8b01121",
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Atom efficient synthesis of selectively difluorinated carbocycles through a gold(I) catalyzed cyclization. / McCarter, Adam W.; Sommer, Magdalana; Percy, Jonathan M.; Jamieson, Craig; Kennedy, Alan R.; Hirst, David J.

In: Journal of Organic Chemistry, 06.07.2018.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Atom efficient synthesis of selectively difluorinated carbocycles through a gold(I) catalyzed cyclization

AU - McCarter, Adam W.

AU - Sommer, Magdalana

AU - Percy, Jonathan M.

AU - Jamieson, Craig

AU - Kennedy, Alan R.

AU - Hirst, David J.

PY - 2018/7/6

Y1 - 2018/7/6

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AB - The intramolecular carbocyclization of difluorinated enol acetals has been achieved for the first time using gold(I) catalysis. Difluorinated enol acetals bearing a pendant alkene group can be cyclized and reduced in one pot to form fluorinated diol motifs. Alternatively, the cyclization of terminal alkynes allows for the synthesis of fluorinated pyran scaffolds. Both cyclization processes can be performed under mild conditions allowing access to complex products rich in functionality. The cyclic systems are synthesized concisely (maximum four steps) from trifluoroethanol, an inexpensive fluorinated feedstock.

KW - gold(I) catalysis

KW - cyclization processes

KW - synthesis

UR - https://pubs.acs.org/journal/joceah

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