Unknown

Dataset Information

0

Synthesis of Unsaturated Silyl Heterocycles via an Intramolecular Silyl-Heck Reaction.

ABSTRACT: We report the synthesis of unsaturated silacycles via an intramolecular silyl-Heck reaction. Using palladium catalysis, silicon electrophiles tethered to alkenes cyclize to form 5- and 6-membered silicon heterocycles. The effects of alkene substitution and tether length on the efficiency and regioselectivity of the cyclizations are described. Finally, through the use of an intramolecular tether, the first examples of disubstituted alkenes in silyl-Heck reactions are reported.

SUBMITTER: Reid WB 

PROVIDER: S-EPMC7236810 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Synthesis of Unsaturated Silyl Heterocycles <i>via</i> an Intramolecular Silyl-Heck Reaction.

Reid William B WB   McAtee Jesse R JR   Watson Donald A DA  

Organometallics 20190926 19

We report the synthesis of unsaturated silacycles <i>via</i> an intramolecular silyl-Heck reaction. Using palladium catalysis, silicon electrophiles tethered to alkenes cyclize to form 5- and 6-membered silicon heterocycles. The effects of alkene substitution and tether length on the efficiency and regioselectivity of the cyclizations are described. Finally, through the use of an intramolecular tether, the first examples of disubstituted alkenes in silyl-Heck reactions are reported. ...[more]

Similar Datasets

Unknown Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.
| S-EPMC5395365 | biostudies-literature
Unknown Preparation of vinyl silyl ethers and disiloxanes via the silyl-Heck reaction of silyl ditriflates.
| S-EPMC3816510 | biostudies-literature
Unknown Endo-selective Pd-catalyzed silyl methyl Heck reaction.
| S-EPMC4291758 | biostudies-literature
Unknown Simplified Preparation of Trialkylvinylsilanes via the Silyl-Heck Reaction Utilizing a Second Generation Catalyst.
| S-EPMC4912221 | biostudies-literature
Unknown Heterocycles via intramolecular platinum-catalyzed propargylic substitution.
| S-EPMC3126105 | biostudies-literature
Unknown Oxacycle synthesis via intramolecular reaction of carbanions and peroxides.
| S-EPMC4004269 | biostudies-literature
Unknown A bifunctional iminophosphorane squaramide catalyzed enantioselective synthesis of hydroquinazolines <i>via</i> intramolecular aza-Michael reaction to α,β-unsaturated esters.
| S-EPMC8098679 | biostudies-literature
Unknown Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (+/-)-gelsemine.
| S-EPMC2597289 | biostudies-literature
Unknown Synthesis of crispine A analogues via an intramolecular Schmidt reaction.
| S-EPMC2213660 | biostudies-literature
Unknown Diastereoselection in the formation of spirocyclic oxindoles by the intramolecular Heck reaction.
| S-EPMC2585599 | biostudies-literature