71832-02-5Relevant academic research and scientific papers
Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2as Sole Reductant
Zhou, Xibing,Zhang, Guoying,Huang, Renbin,Huang, Hanmin
supporting information, p. 365 - 369 (2021/01/26)
Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.
Synthetic and mechanistic studies in enantioselective allylic substitutions catalysed by palladium complexes of a modular class of axially chiral quinazoline-containing ligands
Carroll, Anne-Marie,McCarthy, Mary,Lacey, Patrick M.,Saunders, Cormac P.,Connolly, David J.,Farrell, Annette,Rokade, Balaji V.,Goddard, Richard,Fristrup, Peter,Norrby, Per-Ola,Guiry, Patrick J.
, (2019/12/09)
The application of palladium complexes of a modular series of axially chiral phosphinamine ligands, the Quinazolinaps, to the enantioselective alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate and methyl dimethyl malonate is described.
Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether
Hari Babu, Madala,Ranjith Kumar, Gadi,Kant, Ruchir,Sridhar Reddy, Maddi
supporting information, p. 3894 - 3897 (2017/04/04)
Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units. The apparent vinylnickel intermediate was successfully trapped by the Michael electrophiles to get defined tri- and tetra-substituted olefins. An interesting selectivity switch was observed with internal alkynes.
One-point binding ligands for asymmetric gold catalysis: Phosphoramidites with a TADDOL-related but acyclic backbone
Teller, Henrik,Corbet, Matthieu,Mantilli, Luca,Gopakumar, Gopinadhanpillai,Goddard, Richard,Thiel, Walter,Fuerstner, Alois
supporting information, p. 15331 - 15342 (2012/11/07)
Readily available phosphoramidites incorporating TADDOL-related diols with an acyclic backbone turned out to be excellent ligands for asymmetric gold catalysis, allowing a number of mechanistically different transformations to be performed with good to outstanding enantioselectivities. This includes [2 + 2] and [4 + 2] cycloadditions of ene-allenes, cycloisomerizations of enynes, hydroarylation reactions with formation of indolines, as well as intramolecular hydroaminations and hydroalkoxylations of allenes. Their preparative relevance is underscored by an application to an efficient synthesis of the antidepressive drug candidate (-)-GSK 1360707. The distinctive design element of the new ligands is their acyclic dimethyl ether backbone in lieu of the (isopropylidene) acetal moiety characteristic for traditional TADDOLs. Crystallographic data in combination with computational studies allow the efficiency of the gold complexes endowed with such one-point binding ligands to be rationalized.
Titanocene(II)-promoted stereoselective alkenylation utilizing (Z)-alkenyl sulfones
Ogata, Akitoshi,Nemoto, Masami,Kobayashi, Kenji,Tsubouchi, Akira,Takeda, Takeshi
, p. 3816 - 3822 (2008/02/02)
(Chemical Equation Presented) The stereoselective alkenylation of unsaturated compounds by means of a (Z)-alkenyl sulfone-titanocene-(II) system is described. Treatment of alkynes and (Z)-alkenyl methyl sulfones with the titanocene(II) reagent Cp2Ti[P(OEt)3]2 produced conjugated dienes. This alkenylation system is also applicable to polar C=O bonds; the simple mixing of carbonyl compounds, (Z)-alkenyl methyl sulfones, and the titanocene-(II) reagent formed allylic alcohols. The advantages of alkenylation are that it requires no prepreparation of the alkenylmetal reagent and that it proceeds with complete stereoselectivity.
Selective reduction of alkynes to Z-alkenes using hydrosilane functions immobilized on silica gel
Kini, Abhay D.,Nadkarni, Durgesh V.,Fry, James L.
, p. 1507 - 1510 (2007/10/02)
A solid reagent consisting of hydrosilane functions immobilized on the surface of silica gel was used in conjunction with acetic acid and tetrakis(triphenylphosphine)palladium(0) catalyst to effect the reduction of alkynes to Z-olefins. Simple filtration provides a convenient means for the reaction workup and isolation of products.
Ring-Opening of Isoxazolidine Nucleus by Trimethyl Phosphate Treatment: Formation of Tertiary Allylic Alcohols via Intermediate 1,3-Oxazinium Salts
Chiacchio, Ugo,Liguori, Angelo,Romeo, Giovanni,Sindona, Giovanni,Uccella, Nicola
, p. 799 - 817 (2007/10/02)
5,5-Disubstituted isoxazolidines undergo ring opening reaction, leading to tertiary allylic alcohols, by sequential treatment with trimethyl phosphate (TMP) and NaH.The reaction proceeds through sequence steps which involve an initial alkylation to isoxaz
Mechanism of the Grignard Adddition Reaction. XVI. Homolytic and Concerted Mechanisms in the Reaction of α,β-Unsatureted Carbonyl Compounds with Grignard Reagents
Holm, Torkil
, p. 925 - 929 (2007/10/02)
Kinetic measurements have shown that the addition of Grignard reagents to α,β-unsaturated carbonyl compounds takes place either by a concerted mechanism or by a homolytic mechanism.Phenylmagnesium bromide, which is incapable of homolysis, reacts rapidly in a 1,4-fashion if an s-cis conformation exists between the C=C and the C=O bonds, but only 1,2-addition takes place if the conformation is s-trans.tert-Butylmagnesium bromide is unsuited to the concerted reaction, but 1,4-addition takes place via homolysis.Primary and secondary Grignard reagents, like phenyl, react rapidly in a concerted manner with s-cis substrates, but unlike phenyl, these Grignard reagents may, with s-trans substrates, produce some 1,4-adduct via the homolytic mechanism.
Reactions of Carbonyl Compounds with Grignard Reagents in the Presence of Cerium Chloride
Imamoto, Tsuneo,Takiyama, Noboyuki,Nakamura, Kimikazu,Hatajima, Toshihiko,Kamiya, Yasuo
, p. 4392 - 4398 (2007/10/02)
The addition of Grignard reagents to ketones is significantly enhanced by cerium chloride with remarkable supression of side reactions, particularly enolization.Some esters, which are prone to side reactions, also react readily with Grignard reagents in the presence of cerium chloride to give normal reaction products in reasonable to high yields.
C-C Bond Cleavage and Deoxygenation of Chalcone by the Organo-ytterbium ?-Complex PhYbI
Hou, Zhaomin,Mine, Norioki,Fujiwara, Yuzo,Taniguchi, Hiroshi
, p. 1700 - 1702 (2007/10/02)
Reaction of excess of the organo-ytterbium ?-complex PhYbI with chalcone gives trans-stilbene (1), the C-C bond cleavage product and 1,1,3-triphenylpropene (2) together with diphenylmethanol (3); a possible mechanism of the reaction is proposed.
