71911-76-7

Upstream product

• 934-56-5 trimethyl(phenyl)stannane 
• 6705-51-7 3,4-epoxycyclohexene 
• 51171-72-3 4-phenylcyclohex-2-en-1-one 
• 143365-54-2 trimethyl(([1,2,3,6-tetrahydro-1,1′-biphenyl]-4-yl)oxy)silane 
• 98-80-6 phenylboronic acid 
• 57466-29-2 cis-2-cyclohexene-1,4-diol monoacetate 

Downstream Products

• 51171-72-3 4-phenylcyclohex-2-en-1-one 

Relevant academic research and scientific papers

Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones

Selectivity between 1,2 and 1,4 addition of a nucleophile to an α,β-unsaturated carbonyl compound has classically been modified by the addition of stoichiometric additives to the substrate or reagent to increase their “hard” or “soft” character. Here, we demonstrate a conceptually distinct approach that instead relies on controlling the coordination sphere of a catalyst with visible light. In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β-unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4-selective hydroboration, providing a straightforward and stereoselective route to rare syn-aldol products in one-pot. DFT calculations and mechanistic experiments confirm two different mechanisms are operative, underpinning this unusual photocontrolled selectivity switch.

Palladium pincer complex catalyzed cross-coupling of vinyl epoxides and aziridines with organoboronic acids

Palladium-catalyzed crosscoupling of vinyl epoxides and aziridines with organoboronic acids was performed by using 0.5-2.5 mol % pincer-complex catalyst. The reactions proceed under mild conditions affording allyl alcohols and amines with high regioselectivity and in good to excellent yields. Under the applied reaction conditions aromatic chloro-, bromoand iodo substituents are tolerated. Our results indicate that the mechanism of the pincer complex catalyzed and the corresponding palladium(O) catalyzed process is substantially different. It was concluded that the transformations proceed via transmetalation of the organoboronic acids to the pincercomplex catalyst followed by an S N2′type opening of the vinyl epoxide or aziridine substrate. In this process the palladium atom is kept in oxidation state +2 under the entire catalytic process, and therefore oxidative side reactions can be avoided.

Installation of carbon chain onto 2-cyclohexene-1,4-diol monoacetate

Alkylation of cyclohexenyl monoacetate 1 with R2Cu(CN)(MgCl)2 or RMgBr/CuCN (cat.) in Et2O produced trans 1,2-isomers 4, while arylation and alkenylation of 1 was accomplished with lithium borates 5 and a nickel cat. to af

PALLADIUM CATALYZED COUPLING OF ORGANOSTANNANES WITH VINYL EPOXIDES

The coupling reaction of organotin reagents with vinyl epoxides, catalyzed by palladium, takes place at ambient temperatures, regioselectively, giving predominately the 1,4-addition product.Both aryl- and vinylstannanes undergo coupling in high yields, wh