Unknown

Dataset Information

0

Arylethyne Bromoboration-Negishi Coupling Route to E- or Z-Aryl-Substituted Trisubstituted Alkenes of ?98% IsomericPurity. New Horizon in the Highly Selective Synthesis of Trisubstituted Alkenes.

ABSTRACT: The hitherto unprecedented palladium-catalyzed cross-coupling of (Z)-?-bromo-?-arylethenylboranes can be made to proceed satisfactorily through (1) the use of highly catalytically active bis(tri-tert-butylphosphine)palladium or dichloro[N,N-bis-(2,6-diisopropylphenyl)imidazol-2-yl](m-chloropyridine)palladium and (2) conversion of dibromoboryl group to (pinacol)boryl group. Thus, a wide variety of carbon groups can be used to substitute bromine in ?98% stereo- and regioselectivity, while suppressing the otherwise dominant ?-debromoboration. Together with the alkylethyne-based protocols, the alkyne bromoboration-Negishi coupling tandem process has emerged as the most widely applicable and highly selective route to trisubstituted alkenes including those that are otherwise difficult to access.

SUBMITTER: Wang C 

PROVIDER: S-EPMC3781582 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Arylethyne Bromoboration-Negishi Coupling Route to <i>E</i>- or <i>Z</i>-Aryl-Substituted Trisubstituted Alkenes of ≥98% IsomericPurity. New Horizon in the Highly Selective Synthesis of Trisubstituted Alkenes.

Wang Chao C   Xu Zhaoqing Z   Tobrman Tomas T   Negishi Ei-Ichi EI  

Advanced synthesis & catalysis 20100301 4

The hitherto unprecedented palladium-catalyzed cross-coupling of (<i>Z</i>)-β-bromo-β-arylethenylboranes can be made to proceed satisfactorily through (1) the use of highly catalytically active bis(tri-<i>tert</i>-butylphosphine)palladium or dichloro[<i>N</i>,<i>N</i>-bis-(2,6-diisopropylphenyl)imidazol-2-yl](<i>m</i>-chloropyridine)palladium and (2) conversion of dibromoboryl group to (pinacol)boryl group. Thus, a wide variety of carbon groups can be used to substitute bromine in ≥98% stereo- a  ...[more]

Similar Datasets

Unknown Highly(?98%) Stereo- and Regioselective Trisubstituted Alkene Synthesis of Wide Applicability via 1-Halo-1-alkyne Hydroboration-Tandem Negishi-Suzuki Coupling or Organoborate Migratory Insertion Protocol.
| S-EPMC3781585 | biostudies-literature
Unknown Diastereoselective Coupling of Chiral Acetonide Trisubstituted Radicals with Alkenes.
| S-EPMC4978530 | biostudies-literature
Unknown Highly(?98%) Selective Trisubstituted Alkene Synthesis of Wide Applicability via Fluoride-Promoted Pd-Catalyzed Cross-Coupling of Alkenylboranes.
| S-EPMC3747006 | biostudies-literature
Unknown Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling.
| S-EPMC2766167 | biostudies-literature
Unknown Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.
| S-EPMC2746668 | biostudies-literature
Unknown Nickel-catalyzed Negishi cross-coupling reactions of secondary alkylzinc halides and aryl iodides.
| S-EPMC6474776 | biostudies-literature
Unknown Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids.
| S-EPMC4866599 | biostudies-literature
Unknown Highly stereo- and regioselective synthesis of (Z)-trisubstituted alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling.
| S-EPMC3891656 | biostudies-literature
Unknown Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes.
| S-EPMC2846594 | biostudies-literature
Unknown Stereospecific cross-coupling reactions of aryl-substituted tetrahydrofurans, tetrahydropyrans, and lactones.
| S-EPMC4210078 | biostudies-other