CsOH-promoted P-alkylation: a convenient and highly efficient synthesis of tertiary phosphines

Honaker, Matthew T.; Sandefur, Benjamin J.; Hargett, James L.; McDaniel, Alicia L.; Salvatore, Ralph Nicholas

doi:10.1016/j.tetlet.2003.09.117

Cited by 49 publications

(22 citation statements)

References 25 publications

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“…Salvatore et al described an efficient coupling of secondary phosphines with alkyl halides using CsOH·H 2 O as base. 8 (H) In the literature there is a range of methods for the preparation of stereo-defined trisubstituted alkenes which are a significant group of building blocks in natural products. CsOH·H 2 O in catalytic amount promoted the dimerization of Baylis-Hillman adducts which result in the formation of unsymmetrical bis-allyl ethers consisting of an E-allylic unit and a terminal allylic unit as the only product.…”

Section: Abstractsmentioning

confidence: 99%

CsOH×H2O in Organic Synthesis

Siopa¹

2009

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research CsOH⋅H 2 O in Organic SynthesisCompiled by Filipa Siopa Filipa Siopa was born in Portugal. She received her chemistry degree from Faculdade de Ciências of Universidade de Lisboa in 2003, and is now working towards her PhD under the supervision of Prof. Paula Branco at the Faculdade de Ciências e Tecnologia of Universidade Nova de Lisboa. Her current research is focused on understanding the role of catecholamines in several biological processes, namely the synthesis of catecholamine adducts of amino acids, nucleosides, and small peptides.

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Section: Abstractsmentioning

confidence: 99%

CsOH×H2O in Organic Synthesis

Siopa¹

2009

Synlett

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“…1) of both parent MCM-41 (a) and MPrPPh 2 Rh (b) revealed three well-resolved reflections with Miller Indexes (100), (110), and (200), characteristic of typical hexagonal structure. The d 100 reflection is associated with the pore size of the material with the hexagonal symmetry by the equation [9]:…”

Section: Xrd Characterizationmentioning

confidence: 99%

“…One reason might be that rhodium was anchored to the support by Rh-N coordination. It is well acknowledged in the organometallic chemistry, phenyl phosphine ligands are very effective in forming stable transition metal complexes [9] owing to the conjunction of phosphorous p electrons with phenyl p electrons. So far, few researchers have devoted to the direct anchor of rhodium complex to phosphino-functionalized mesoporous silicate.…”

Section: Introductionmentioning

confidence: 99%

Anchoring RhCl(CO)(PPh3)2 to –PrPPh2 Modified MCM-41 as Effective Catalyst for 1-Octene Hydroformylation

Zhou

2008

Catal Lett

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RhCl(CO)(PPh 3 ) 2 was anchored to diphenylphosphinopropyl-modified (-PrPPh 2 ) mesoporous silicate MCM-41. Infrared spectroscopy was applied to monitor the multi-step assemble of the complex by assigning critical absorptions. The prepared catalyst was employed in 1-octene hydroformylation and showed high conversion of substrate as well as high selectivity of nonyl aldeydes ([97%) along with several stable catalyst cycles. Rhodium leaching in the reaction liquids was determined by mass spectroscopy, which was found extremely low. The catalyst showed higher activity and lower metal loss than the analogue by nano SiO 2 as support, probably as a result of the confining of molecular sieves with ordered pores.

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“…Cesium bases have demonstrated several merits in organic synthetic reactions [28][29][30][31][32][33][34], highlighted by comparative high solubilities [35], appropriate basicities and good stabilities [36][37][38][39][40][41]. In this work, we reported a safe and convenient method for the preparation of a-hydroxyketones from a-haloketones by using cesium formate (HCO 2 Cs).…”

Section: Introductionmentioning

confidence: 99%