The present disclosure is directed to a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by a propargyl alkoxy moiety. Radical translocations lead to the boomerang return of radical center to the site of initial attack where it assists to the elimination of the directing functionality via -scission in the last step of the cascade. In some aspects, the reaction of the present invention is catalyzed by a stannane moiety, which allows further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions.

The present disclosure is directed to a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by a propargyl alkoxy moiety. Radical translocations lead to the boomerang return of radical center to the site of initial attack where it assists to the elimination of the directing functionality via -scission in the last step of the cascade. In some aspects, the reaction of the present invention is catalyzed by a stannane moiety, which allows further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions.

The present disclosure is directed to a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by a propargyl alkoxy moiety. Radical translocations lead to the boomerang return of radical center to the site of initial attack where it assists to the elimination of the directing functionality via -scission in the last step of the cascade. In some aspects, the reaction of the present invention is catalyzed by a stannane moiety, which allows further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions.

In one embodiment, the present application discloses mixtures comprising (a) water in an amount of at least 1% wt/wt of the mixture; (b) a transition metal catalyst; and (c) one or more solubilizing agents; and methods for using such mixtures for performing transition metal mediated bond formation reactions.

In one embodiment, the present application discloses mixtures comprising (a) water in an amount of at least 1% wt/wt of the mixture; (b) a transition metal catalyst; and (c) one or more solubilizing agents; and methods for using such mixtures for performing transition metal mediated bond formation reactions.

In one embodiment, the present application discloses mixtures comprising (a) water in an amount of at least 1% wt/wt of the mixture; (b) a transition metal catalyst; and (c) one or more solubilizing agents; and methods for using such mixtures for performing transition metal mediated bond formation reactions.

In one embodiment, the present application discloses mixtures comprising (a) water in an amount of at least 1% wt/wt of the mixture; (b) a transition metal catalyst; and (c) one or more solubilizing agents; and methods for using such mixtures for performing transition metal mediated bond formation reactions.

The process is provided for forming the reaction product comprising the homologue mixture of I(CF.sub.2).sub.nI, wherein n is 3 to 7, which may contain at least one of the contaminants ICF.sub.2I and I(CF.sub.2).sub.2I, by the steps comprising (a) reacting iodine with hexafluoropropylene oxide at a temperature of 150 C. to 210 C. in a reactor, the amount of said hexafluoro-propylene oxide being a portion of the total amount of hexafluoropropylene oxide to be reacted with said iodine, thereby forming a reaction product containing gaseous perfluoroacetyl fluoride as a reaction by-product, (b) cooling said reaction product to become liquid except for said gaseous perfluoroacetyl fluoride, (c) venting said perfluoroacetyl fluoride from said reactor, and (d) repeating said steps (a), (b), and (c) until said total amount of said HFPO is reacted with said iodine.

The process is provided for forming the reaction product comprising the homologue mixture of I(CF.sub.2).sub.nI, wherein n is 3 to 7, which may contain at least one of the contaminants ICF.sub.2I and I(CF.sub.2).sub.2I, by the steps comprising (a) reacting iodine with hexafluoropropylene oxide at a temperature of 150 C. to 210 C. in a reactor, the amount of said hexafluoro-propylene oxide being a portion of the total amount of hexafluoropropylene oxide to be reacted with said iodine, thereby forming a reaction product containing gaseous perfluoroacetyl fluoride as a reaction by-product, (b) cooling said reaction product to become liquid except for said gaseous perfluoroacetyl fluoride, (c) venting said perfluoroacetyl fluoride from said reactor, and (d) repeating said steps (a), (b), and (c) until said total amount of said HFPO is reacted with said iodine.

The process is provided for forming the reaction product comprising the homologue mixture of I(CF.sub.2).sub.nI, wherein n is 3 to 7, which may contain at least one of the contaminants ICF.sub.2I and I(CF.sub.2).sub.2I, by the steps comprising (a) reacting iodine with hexafluoropropylene oxide at a temperature of 150 C. to 210 C. in a reactor, the amount of said hexafluoro-propylene oxide being a portion of the total amount of hexafluoropropylene oxide to be reacted with said iodine, thereby forming a reaction product containing gaseous perfluoroacetyl fluoride as a reaction by-product, (b) cooling said reaction product to become liquid except for said gaseous perfluoroacetyl fluoride, (c) venting said perfluoroacetyl fluoride from said reactor, and (d) repeating said steps (a), (b), and (c) until said total amount of said HFPO is reacted with said iodine.