M. A. Kazankova

Catalytic Methods for Building up Phosphorus Carbon Bond

The review deals with reactions leading to formation of phosphorus-carbon bonds in the presence of transition metal complexes.

NICKEL- AND PALLADIUM-CATALYZED CROSS-COUPLING AS A ROUTE TO 1- AND 2-ALKOXY- OR DIALKYLAMINOVINYLPHOSPHONATES

1- and 2-alkoxy- or dialkylaminovinylphosphonates were synthesized using reactions of the corresponding vinylhalides with di- and triethylphosphites in the presence of catalytic amounts of Ni salts and Pd complexes. The best way for synthesis of 1-alkoxy or dialkylaminoderivatives is the Pd-catalyzed cross-coupling reaction with (EtO)2POH and the best way for 2-alkoxy- or dialkylaminovinylphosphonates is the Arbuzov reaction with (EtO)3P catalyzed by Ni salts.

Synthesis of vinyldiphenylphosphines by Pd-catalyzed cross-coupling reactions of diphenylphosphine with alkenylhalides

Abstract α- and β-alkoxy (α- and β-dialkylamino)vinylphosphines were synthesized by palladium catalyzed reactions of the corresponding vinylhalides with diphenylphosphine or diphenyltrimethylsilylphosphine in high yields.

Synthesis of Vinylphosphines by Hydrophosphination of Alkynes in the Presence of Transition Metal Complexes

Intermolecular hydrophosphination of terminal and internal alkynes with diphenylphosphine, catalyzed by palladium and nickel complexes, was accomplished for the first time. The reaction follows the syn-addition pattern. Conditions were found which ensure regioselective addition with predominant or exclusive formation of the corresponding α- or β-adduct.

Cross-coupling of E,E-1,4-diiodobuta-1,3-diene with nucleophiles catalyzed by Pd or Ni complexes: a new route to functionalized dienes

E,E-1,4-Diiodobuta-1,3-diene can enter into cross-coupling reactions with carbon- or other element-centered nucleophiles in the presence of Pd or Ni complexes as catalysts. Convenient procedures were developed for the stereoselective synthesis of E,E-1,4-dialkenylbuta-1,3-dienes, dienyl-1,4-bisphosphonates, E,E-1,4-bis(diphenylphosphino)buta-1,3-diene, E,E-1,4-diphenylbuta-1,3-diene, and E,E-1,4-bis(thiophenyl)buta-1,3-diene.

The addition of phosphorus halides to ynamines. Ring-chain tautomerism of phosphirene with isomeric open structure

Abstract The reaction of halogenodiisopropylphosphines 3a-c with 1-diethylamino- 1-butyne 4 in dichloromethane leads to new phosphirenes 5. In benzene or pentane mixtures of phosphirines 5c and isomeric open structure 6 have been obtained. Ring-chain tautomerism for 5c and 6 have been observed for the first time.

Hydrophosphination of alkoxyalkenes catalyzed by transition metal complexes

Diphenylphosphine adds to alkyl vinyl ethers in the presence of Ni(II) and Pd(II) complexes with a high regioselectivity, leading to exclusive formation of the corresponding Markownikoff adducts which were isolated as 1-alkoxyalkyl(diphenyl)phosphine oxides via oxidation with hydrogen peroxide.

Competitive addition and cycloaddition of low coordinated organophosphorus compounds to alkoxy- and aminoalkynes

Abstract Reactions of two- and three coordinated organophosphorus compounds with nucleophilic alkynes can proceed as competitive addition, [2+1]-, and [2+2]- cycloaddition reactions. Ring-chain tautomerism for phosphirenes and isomeric alkenylphosphines has been observed.

Synthesis of alkyl(diphenyl)phosphines by hydrophosphination of vinylarenes catalyzed by transition metal complexes

Hydrophosphination of styrenes and their heteroanalogs with diphenylphosphine in the presence of nickel or palladium complexes was accomplished for the first time. The reaction ensures high yields and regioselectivity: the corresponding anti-Markownikoff adducts are exclusively formed.

Transition metal-catalyzed cross-coupling of 1,4-diiodobutadienes with thiols—A novel route to 1,4-bis(R-sulfanyl)buta-1,3-dienes

Cross-coupling of 1,4-diiodobuta-1,3-dienes with thiols in the presence of Pd, Ni, and Cu complexes gives 1,4-bis[aryl(alkyl)sulfanyl]buta-1,3-dienes in high yields.