Convenient procedure for the syntheses of vinyl iodides via the reaction of iodine monochloride with vinylboronic acids

Technical Report · Tue Jan 01 04:00:00 EST 1980

DOI:https://doi.org/10.2172/6699281· OSTI ID:6699281

Kabalka, G. W.; Gooch, E. E.; Hsu, H. C.

Vinyl halides are important synthetic intermediates. One route to vinyl halides involves the reaction of vinylboronic acids with halogens in the presence of sodium hydroxide. Although the reaction of iodine with organoborane reagents has been carefully investigated and is known to produce good yields of stereochemically defined products, it does have two potential disadvantages. The first is the necessity of using a strong base which could react with sensitive functional groups. The second is the fact that one-half of the iodine molecule is lost as iodide which is not economical when radionuclides of iodine are employed. An alternative method of preparing vinyl halides is reported in this paper. Vinyl boronic acids (readily prepared via the hydroboration of alkynes) react with iodine monochloride to yield the corresponding vinyl iodides. This reaction is applicable to a variety of functionally substituted materials. The reaction of triphenylborane with iodine monochloride is also reported.

• Research Organization: Tennessee Univ., Knoxville (USA). Dept. of Chemistry
• Sponsoring Organization: USDOE
• DOE Contract Number: AS05-80EV10363
• OSTI ID: 6699281
• Report Number(s): DOE/EV/10363--1
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
AROMATICS
BORANES
BORON COMPOUNDS
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
IODINATED ALIPHATIC HYDROCARBONS
IODINATED AROMATIC HYDROCARBONS
IODINE CHLORIDES
IODINE COMPOUNDS
ORGANIC BORON COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
SYNTHESIS