182153-21-5

Upstream product

• 19814-75-6 9,9-dimethylxanthene 

Downstream Products

• 2160535-56-6 C₃₉H₄₀NO₃PS 
• 2162939-89-9 (R)-N-((S)-1-(5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl)-2,2-dimeth ylpropyl)-2-methylpropane-2-sulfinamide 
• 2162939-89-9 (R)-N-((R)-1-(5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl)-2,2-dimeth ylpropyl)-2-methylpropane-2-sulfinamide 
• 2374225-98-4 (Rs)-N-((Sc)-(5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl)(o-tolyl)methyl)-2-methylpropane-2-sulfinamide 
• 2160535-59-9 (Ss)-N-((Rc)-(4-(tert-butyl)phenyl)(5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl)methyl)-2-methylpropane-2-sulfinamide 
• 1333321-80-4 4-(diphenylphosphanyl)-9,9-dimethylxanthene 

Relevant academic research and scientific papers

Gold-Catalyzed Asymmetric Intramolecular Cyclization of N-Allenamides for the Synthesis of Chiral Tetrahydrocarbolines

Highly enantioselective gold-catalyzed intramolecular cyclization of N-allenamides was implemented by utilizing a designed chiral sulfinamide phosphine ligand (PC-Phos). This represents the first example of highly enantioselective intramolecular cyclization of N-allenamides. The practicality of this reaction was validated in the total synthesis of (R)-desbromoarborescidine A and formal synthesis of (R)-desbromoarborescidine C and (R)-deplancheine. Moreover, the catalyst system PC-Phos/AuNTf2 proved to be specifically efficient to promote the desymmetrization of N-allenamides in excellent yields with satisfactory ee values.

Macrocycle Formation by Cooperative Selection at a Double-Sited Frustrated Lewis Pair

Hydroboration of the 4,5-bis(allyl,mesityl)phosphanyl xanthene derivative 2 with Piers' borane [HB(C6F5)2] gave the bis-P/B frustrated Lewis pair 3. In this situation, the two symmetry-equivalent P/B FLP units featured markedly different reaction modes. With resorcinol, they formed the 20-membered macrocycle 11 by a sequence of -OH deprotonation/borane-induced tautomerization. With aryl acetylenes, the 18-membered macrocyclic products 15 (three examples) were formed in a unique sequence of carbon-carbon coupling reactions.

Structurally strained cyclic xanthene dimers: A model for the rigid crown ether moiety in the reduced graphene oxide framework

Highly strained cyclic xanthene dimers, which serve as models for reduced graphene oxide (RGO), were synthesized by Ni(0) mediated homo-coupling reactions. The dimers are obtained as highly stable colorless solids. X-ray crystallographic analysis of a tetra-tert-butyl derivative demonstrates that it possesses a highly strained structure with an extremely short non-bonded O￡O distance (2.5662(44) ?). The results of variable temperature NMR experiments show that no signal broadening occurs even at 398 K, indicating that conformational flipping requires considerably high energy.

Asymmetric Dearomatization of Indole by Palladium/PC-Phos-Catalyzed Dynamic Kinetic Transformation

A palladium-catalyzed intermolecular dynamic kinetic asymmetric dearomatization of 3-arylindoles with internal alkynes was developed with the use of achiral Xantphos and chiral sulfinamide phosphine ligand (PC-Phos) as the co-ligands. This method could deliver various spiro[indene-1,3′-indole] compounds in good yields (up to 95 % yield) with up to 98 % ee. The salient features of the transformation include the use of readily available substrates, ease of scale-up and the versatile functionalization of the products. The mechanistic experiments gave some insights on active intermediates.

Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications

Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.