63886-54-4

Upstream product

• 111-66-0 oct-1-ene 
• 18108-09-3 butyl hypophosphite 
• 629-27-6 1-Iodooctane 
• 111-83-1 1-bromo-octane 

Relevant academic research and scientific papers

Palladium-catalyzed hydrophosphinylation of alkenes and alkynes

Various palladium catalysts promote the addition of hypophosphorous derivatives ROP(O)H2 to alkenes and alkynes in good yields and under mild conditions. Particularly, Cl2Pd(PPh3)2/2 MeLi, and Pd2dba3/xantphos allow for phosphorus-carbon bond formation instead of transfer hydrogenation. Commercial aqueous solutions of hypophosphorous acid can be employed successfully at ambient temperature. With styrene and terminal alkynes, the regioselectivity (linear versus branched products) can be controlled to some extent with the catalytic system employed. The methodology considerably extends upon previous routes for the preparation of H-phosphinic acids and other organophosphorus compounds. Copyright

Hydrophosphinylation of unactivated terminal alkenes catalyzed by nickel chloride

The room-temperature hydrophosphinylation of unactivated monosubstituted alkenes using phosphinates (ROP(O)H2) and catalytic NiCl2 in the presence of dppe is described. The method is competitive with prior palladium-catalyzed reactio

Direct monoalkylation of alkyl phosphinates to access H-phosphinic acid esters

Simple alkyl phosphinates prepared by the silicate esterification method can be alkylated under Barbier-like conditions with butyl lithium at -78 °C followed by warming to room temperature. The method is limited to the more reactive electrophile such as allylic bromides and alkyl iodides. With these electrophiles good yields of H-phosphinic acid esters are generally obtained in a straightforward manner. Georg Thieme Verlag Stuttgart.

Recent advances in phosphorus-carbon bond formation: Synthesis of H-phosphinic acid derivatives from hypophosphorous compounds

This account summarizes the research conducted in our laboratory over the past five years. New methodologies were devised for the formation of P-C bonds with a focus on the reactions of hypophosphorous acid derivatives. Three types of reactions have been developed: palladium-catalyzed cross-coupling, room-temperature radical addition, and palladium-catalyzed addition. Our results are summarized in each of these areas and include some of our most recent data. (1) Our palladium-catalyzed cross-coupling has been extended to the direct coupling of alkyl phosphinates with a variety of aryl, heteroaryl, and even alkenyl electrophiles. (2) The addition of sodium hypophosphite under radical conditions is extended from alkenes to alkynes. (3) The catalytic addition of hypophosphorous compounds using palladium catalysts (hydrophosphinylation) is also discussed.