Pd-Catalyzed C-3 functionalization of indolizines via C-H bond cleavage.
Summary of "Pd-Catalyzed C-3 functionalization of indolizines via C-H bond cleavage."
New transition metal-catalyzed methods for the arylation of indolizines by the direct cleavage of C-H bonds have been developed. A wide range of aryltrifluoroborate salts react with indolizines in the presence of Pd(OAc)(2) catalyst and AgOAc oxidant to give the arylated indolizines in high yields. Both electron-donating and electron-withdrawing groups perform smoothly while bromide and chlorine substituents are tolerated. In addition, the indolizines display similar reactivities in the Pd-catalyzed reaction with 3-phenylpropiolic acid to afford the corresponding C-3 alkynylated indolizines. These methods allow the direct functionalization of indolizines in one step.
Affiliation
Institute of Applied Chemistry and Department of Chemistry, University of Shaoxing, Shaoxing, Zhejiang Province 312000, People's Republic of China. babygarfield@126.com.
Journal Details
This article was published in the following journal.
Name: Organic & biomolecular chemistry
ISSN: 1477-0539
Pages: 7108-19
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22868382
- DOI: http://dx.doi.org/10.1039/c2ob25643f
Medical and Biotech [MESH] Definitions
Dna Cleavage
A reaction that severs one of the covalent sugar-phosphate linkages between NUCLEOTIDES that compose the sugar phosphate backbone of DNA. It is catalyzed enzymatically, chemically or by radiation. Cleavage may be exonucleolytic - removing the end nucleotide, or endonucleolytic - splitting the strand in two.
Phosphonic Acids
Inorganic or organic derivatives of phosphonic acid with the general formula ROP(OH)2 or RP(=O)(OH)2. The tautomeric form of this compound (P(OH)3) is PHOSPHOROUS ACIDS. Nucleoside phosphonates have a phosphate-carbon bond that is more resistant to enzymatic cleavage than the normal phosphate-oxygen bond.
Photolysis
Chemical bond cleavage reactions resulting from absorption of radiant energy.
Cleavage Stimulation Factor
A RNA-binding protein that stimulates the cleavage of the 3' end of MRNA near the POLYADENYLATION site. It is a heterotrimer of 55-, 64- and 77-kDa subunits and combines with CLEAVAGE STIMULATION FACTOR to form a stable complex with mRNA that directs the 3' cleavage and polyadenylation reaction.
PubMed Articles
A novel palladium-catalyzed C-3 acylation of indolizines with α,β-unsaturated carboxylic acids via C-H bond and C═C double bond cleavage under oxidative conditions is described. The regioselectivi...
An efficient synthetic method for producing indolizines through a tandem Pd-catalyzed selective allenyl cross-coupling reaction using organoindium reagents and cycloisomerization was developed in a on...
C-h bond functionalization in the synthesis of fused 1,2,3-triazoles.
A highly modular approach to fused 1,2,3-triazoles has been developed featuring a one-pot procedure combining copper(I) catalyzed azide-alkyne cycloaddition and palladium-catalyzed C-H bond functional...
To demonstrate the utility of isocyanides in catalytic C-H bond functionalization reactions, a palladium-catalyzed cyclocoupling reaction of 2-halobiaryls with isocyanides was developed. The reaction...
Triple bonds do it! The molybdenum-catalyzed CN bond cleavage of organic amides with hydrosilanes to produce alcohols and amines has been investigated. This work complements previously established...
Clinical Trials
Validation of Brief Objective Neurobehavioral Detectors (BOND) in Mild TBI
The Veterans Health Administration (VHA) has stated the need for a brief screening instrument that can assist with the triage of the enormous number of returning OEF/OIF veterans with conc...
Clinical Evaluation of Three Dental Adhesive Systems in Class V Restorations
The purpose of this study is to compare the clinical performance of three dental adhesive systems used to bond Class V cavity fillings in adult teeth.
Efficacy of Brooke Bond Black Tea Extract on Flow Mediated Dilation in Indian Males
This study examines the effect of 1800 mg/day standardized Brooke Bond black tea extract, equivalent to 400 mg flavonoids, on Flow Mediated Dilation in healthy Indian males.
Identification of Viable Human Embryos Using Three Different Methods
Infertility affects an increasing number of couples. For many, the choice of treatment is in vitro fertilization (IVF) . Currently, there are no markers fully predictive of developmental c...
Study of Assisted Hatching of Cleavage Stage Embryos
The purpose of this study was to determine if assisted embryo hatching can improve pregnancy rates for good prognosis patients undergoing in vitro fertilization (IVF) with day 3 embryo tra...
