Regioselective Suzuki couplings of non-symmetric dibromobenzenes: alkenes as regiochemical control elements.
نویسندگان
چکیده
The regiochemical outcome of Suzuki couplings of non-symmetric dibromobenzenes is investigated. Selectivities are dependent on the proximity of the bromine atom to alkene substituents, not on steric or electronic effects. Extension to a one-pot three-component Suzuki reaction leads to efficient terphenyl syntheses.
منابع مشابه
Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction.
[reaction: see text]Transannular macrocyclizations via intramolecular B-alkyl Suzuki reactions are described. Regioselective terminal olefin hydroboration with 9-BBN followed by Pd(0)-catalyzed Suzuki reaction in the presence of a base such as TlOEt at high dilution generates macrocycles with a high degree of control over olefin geometry with isomerically pure E or Z vinyl iodide substrates. Th...
متن کاملSynthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.
Copper-catalyzed functionalization of terminal or 1,1-disubstituted alkenes with bis(pinacolato)diboron and methanol provides formal hydroboration products with exceptional regiocontrol favoring the branched isomer. Pairing this procedure with photocatalytic cross-couplings using iridium and nickel cocatalysis provides an effective, highly regioselective procedure for the hydroarylation of term...
متن کاملOne-pot multicomponent click synthesis of some novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes
A facile and one-pot multicomponent synthesis of novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes at room temperature is reported. At the first step, in the presence of I2/NaN3 reagents, various alkenes were converted to the corresponding azido iodides and in the next step, the reaction of these compounds with phenylacetylene in the presence of catalytic amount of sodium ascorbate/ CuSO4...
متن کاملEnantioselective and regioselective pyrone Diels-Alder reactions of vinyl sulfones: total synthesis of (+)-cavicularin.
The total synthesis of (+)-cavicularin is described. The synthesis features an enantio- and regioselective pyrone Diels-Alder reaction of a vinyl sulfone to construct the cyclophane architecture of the natural product. The Diels-Alder substrate was prepared by a regioselective one-pot three-component Suzuki reaction of a non-symmetric dibromoarene.
متن کاملCopper-catalyzed regioselective ortho C-H cyanation of vinylarenes.
A copper-based catalytic technique for the regioselective ortho C-H cyanation of vinylarenes has been developed. This method provides an effective means for the selective functionalization of vinylarene derivatives. A copper-catalyzed cyanative dearomatization mechanism is proposed to account for the regiochemical course of this reaction.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 13 22 شماره
صفحات -
تاریخ انتشار 2015