A Convenient Large-Scale Synthesis of Cyclobutyl Halides

Dupont, Andrea C.; Audia, Vicki H.; Waid, Philip P.; Carter, J. Paul

doi:10.1080/00397919008052804

Cited by 13 publications

(6 citation statements)

References 16 publications

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Section: Pioneering and Classical Methodsmentioning

confidence: 99%

“…Tetramethylammonium, sodium, potassium, and calcium chlorides give acceptable yields of the corresponding alkyl chloride. While benzene is considered to be the most suitable solvent for the original Kochi reaction, other solvents such acetonitrile, pyridine, and THF could be used in some specific cases. ,, …”

Section: Pioneering and Classical Methodsmentioning

confidence: 99%

“…While benzene is considered to be the most suitable solvent for the original Kochi reaction, other solvents such acetonitrile, pyridine, and THF could be used in some specific cases. 131,140,126 Notably, minor amounts of oxygen readily halt the process, so the reaction must be conducted under an inert atmosphere. Although the reaction does not have to be scrupulously dry, moisture-free solvents were preferred in many cases.…”

Section: Modifications Of the Hunsdiecker−borodin Reactionmentioning

confidence: 99%

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Decarboxylative Halogenation of Organic Compounds

2020

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Decarboxylative halogenation, or halodecarboxylation, represents one of the fundamental key methods for the synthesis of ubiquitous organic halides. The method is based on conversion of carboxylic acids to the corresponding organic halides via selective cleavage of a carbon–carbon bond between the skeleton of the molecule and the carboxylic group and the liberation of carbon dioxide. In this review, we discuss and analyze major approaches for the conversion of alkanoic, alkenoic, acetylenic, and (hetero)aromatic acids to the corresponding alkyl, alkenyl, alkynyl, and (hetero)aryl halides. These methods include the preparation of families of valuable organic iodides, bromides, chlorides, and fluorides. The historic and modern methods for halodecarboxylation reactions are broadly discussed, including analysis of their advantages and drawbacks. We critically address the features, reaction selectivity, substrate scopes, and limitations of the approaches. In the available cases, mechanistic details of the reactions are presented, and the generality and uniqueness of the different mechanistic pathways are highlighted. The challenges, opportunities, and future directions in the field of decarboxylative halogenation are provided.

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Section: Pioneering and Classical Methodsmentioning

confidence: 99%

Section: Pioneering and Classical Methodsmentioning

confidence: 99%

Section: Modifications Of the Hunsdiecker−borodin Reactionmentioning

confidence: 99%

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Decarboxylative Halogenation of Organic Compounds

2020

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“…To cite this article: (1991) Erratum, Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, 21:18-19, 1989-1989, DOI: 10.1080 To link to this article: http://dx.doi.org/10.1080/00397919108021792…”

Section: Erratummentioning

confidence: 96%

Erratum

1991

Synthetic Communications

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“…In this case, aerobic oxidation required elevated temperatures in order to occur. Almost no conversion was detected, if 2-phenylhex-5-en-2-ol (9e) 44 was aerated for 3 h in a solution of 2-propanol at 60 • C in the presence of complex 6. In 2-butanol at 98 • C, 83% conversion of 9e was attainable after a period of 15 h. The reaction afforded 15% of trisubstituted tetrahydrofuran 10e (cis : trans = 20 : 80) and 39% of diol 18 45 (Scheme 2).…”

Section: Stereoselectivitymentioning

confidence: 99%

Activation of molecular oxygen and its use in stereoselective tetrahydrofuran-syntheses from δ,ε-unsaturated alcohols

2008

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Bishomoallylic alcohols (pent-4-en-1-ols) underwent efficient oxidative cyclizations, if treated with O(2) and bis{2,2,2-trifluoromethyl-1-[(1R,4S)-1,7,7-trimethyl-2-(oxo-kappaO)bicyclo[2.2.1]hept-3-yliden]ethanolato-kappaO}cobalt(ii) in solutions of 2-propanol at 60 degrees C. Ring closures occurred diastereoselectively and afforded 2,3-trans- (96% de), 2,4-cis- (approximately 60% de), and 2,5-trans-substituted (>99% de) (phenyl)tetrahydrofur-2-ylmethanols as major components. Formation of bicyclic compounds and a 2,3,4,5-substituted oxolane was feasible as exemplified by syntheses of oxabicyclo[4.3.0]nonylmethanols and a derivative of natural product magnosalicin in 61-72% (90-99% de). The effectiveness of tetrahydrofuran synthesis was critically dependent on (i) solvent, (ii) reaction temperature, (iii) initial cobalt concentration, (iv) chain length between hydroxyl and vinyl groups, and (v) substitution at reacting entities. A sequence is proposed for rationalizing observed selectivities.

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A Convenient Large-Scale Synthesis of Cyclobutyl Halides

Cited by 13 publications

References 16 publications

Decarboxylative Halogenation of Organic Compounds

Decarboxylative Halogenation of Organic Compounds

Erratum

Activation of molecular oxygen and its use in stereoselective tetrahydrofuran-syntheses from δ,ε-unsaturated alcohols

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