skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Fluoride-Assisted Activation of Calcium Carbide: A Simple Method for the Ethynylation of Aldehydes and Ketones

Journal Article · · Organic Letters
 [1];  [2];  [3];  [1]
  1. Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany
  2. Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States
  3. Institute of Inorganic and Analytical Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany

Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
AC02-76SF00515
OSTI ID:
1183811
Journal Information:
Organic Letters, Journal Name: Organic Letters Vol. 17 Journal Issue: 11; ISSN 1523-7060
Publisher:
American Chemical SocietyCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 64 works
Citation information provided by
Web of Science

References (39)

Synthesis of Functional Acetylene Derivatives from Calcium Carbide journal February 2012
Au-Catalyzed Formation of Functionalized Quinolines from 2-Alkynyl Arylazide Derivatives journal August 2013
Steroids. CCVII. Ring A Modified Hormone Analogs. Part III. 1 2-Formyl-Δ 2 -androstenes and Related Compounds. A New Class of Potent Anabolic Agents 2 journal March 1963
From Limestone to Catalysis: Application of Calcium Compounds as Homogeneous Catalysts journal April 2010
A theoretical study of acetone reactions with acetylene and phenylacetylene in the KOH/DMSO superbasic system journal July 2014
Microwave-Accelerated Coupling-Isomerization Reaction (MACIR) – A General Coupling-Isomerization Synthesis of 1,3-Diarylprop-2-en-1-ones journal December 2006
The Reaction of Lithium Acetylide·Ethylenediamine with Ketones journal July 1964
The Nef Reaction with α,β-Unsaturated Ketones journal June 1949
Synthesis of secondary propargyl alcohols from aromatic and heteroaromatic aldehydes and acetylene in the system KOH-H2O-DMSO journal March 2013
Bildung des Acetylens durch Kohlenstoffcalcium journal January 1862
Synthesis and Biological Evaluation of Metabolites of 2- n -Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9 H -purin-6-ylamine (ST1535), A Potent Antagonist of the A 2A Adenosine Receptor for the Treatment of Parkinson’s Disease journal June 2013
Alkynylation of Aldehydes and Ketones Using the Bu 4 NOH/H 2 O/DMSO Catalytic Composition: A Wide-Scope Methodology: Alkynylation of Aldehydes and Ketones journal June 2014
The Relative Reactivity of Various Functional Groups toward a Grignard Reagent journal July 1933
Calcium-Mediated Intramolecular Hydroamination Catalysis journal February 2005
Synthesis of Cyclohexylideneacetaldehyde and 2-, 3- and 4-Methylcyclohexylideneacetaldehyde journal February 1960
THE PREPARATION AND ALKYLATION OF METAL ACETYLIDES IN LIQUID AMMONIA * journal March 1937
The use of calcium carbide in one-pot synthesis of symmetric diaryl ethynes journal January 2006
Syntheses of Xanthofulvin and Vinaxanthone, Natural Products Enabling Spinal Cord Regeneration journal October 2012
Synthesis of acetylenic alcohols with calcium carbide as the acetylene source journal January 2013
Catalytic hydroacetylenation of carbodiimides with homoleptic alkaline earth hexamethyldisilazides journal January 2014
Gold-Catalyzed Tandem [3,3]-Propargyl Ester Rearrangement Leading to ( E )-1 H -Inden-1-ones journal December 2013
Improved synthesis of tertiary propargyl alcohols by the Favorskii reaction of alkyl aryl (hetaryl) ketones with acetylene journal January 2013
Evidence of Solubility of the Acetylide Ion C 2 2− : Syntheses and Crystal Structures of K 2 C 2 ⋅2 NH 3 , Rb 2 C 2 ⋅2 NH 3 , and Cs 2 C 2 ⋅7 NH 3 journal November 2012
Carbonylation of Propargyl Carbamates with Palladium(II) Bisoxazoline Catalysts: Efficient Synthesis of 5-Methoxy-3(2 H )-furanones journal June 2013
A convenient synthesis of hetarylethynyl ketones from hetarylcarbaldehydes and acetylene journal May 2013
1-Ethynylcyclohexanol journal January 1949
Coordination Behavior of Calcocene and Its Use as a Synthon for Heteroleptic Organocalcium Compounds journal March 2011
Facile Synthesis of Halogenated Spiroketals via a Tandem Iodocyclization journal April 2014
Organocatalytic Alkynylation of Aldehydes and Ketones under Phase-Transfer Catalytic Conditions journal June 2005
β-Diketiminato Calcium Acetylides: Synthesis, Solution Dimerization, and Catalytic Carbon−Carbon Bond Formation journal November 2008
Reactions of acetylenes in superbasic media. Recent advances journal July 2014
Direct synthesis of aryl substituted pyrroles from calcium carbide: an underestimated chemical feedstock journal January 2015
Solubility of KF in tributyl phosphate, dimethyl sulfoxide, N,N-dimethylacetamide and 1,4-dioxane from 300.87 to 359.50K journal February 2012
Total Synthesis of Neuroprotectin D1 Analogues Derived from Omega-6 Docosapentaenoic Acid (DPA) and Adrenic Acid (AdA) from a Common Pivotal, Late-Stage Intermediate journal March 2014
Chemical effects of steric strains—XIV journal January 1957
Some organo-compounds of calcium, strontium and barium journal November 1971
Synthesis of Allenes via Gold-Catalyzed Intermolecular Reaction of Propargylic Alcohols and Aromatic Compounds journal March 2012
Production of Acetylene and Acetylene-based Chemicals from Coal journal November 2013
Acetylide Ion (C 2 2− ) as a Synthon To Link Electrophiles and Nucleophiles: A Simple Method for Enaminone Synthesis journal April 2013