49623-06-5

Upstream product

• 66223-54-9 (E)-3-(m-tolyl)acrylaldehyde 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 93614-80-3 3-(3-methylphenyl)prop-2-en-1-al 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 73244-32-3 3-(3-methylphenyl)-2-propen-1-ol 
• 82444-40-4 3-(3-methylphenyl)acrylic acid methyl ester 
• 3029-79-6 3-methylcinnamic acid 
• 1560-54-9 allyltriphenylphosphonium bromide 
• 620-23-5 m-tolyl aldehyde 
• 591-17-3 meta-bromotoluene 
• 1174153-17-3 (E)-1-(2-iodovinyl)-3-methylbenzene 
• 75927-49-0 pinacol vinylboronate 
• 1097191-49-5 1-allyl-2-(3-methylbenzylidene)hydrazine 

Relevant academic research and scientific papers

Ni-Catalyzed Regioselective Hydroarylation of 1-Aryl-1,3-Butadienes with Aryl Halides

An efficient nickel-catalyzed regioselective hydroarylation of 1,3-dienes with aryl halides and a silane has been developed, affording a range of allylic arenes in good to excellent yields under mild conditions. This method exhibits broad substrate scope,

Nickel-catalyzed allyl-allyl coupling reactions between 1,3-dienes and allylboronates

A regiospecific allyl-allyl coupling reaction between 1,3-dienes and allylboronates has been demonstrated under nickel catalysis. Salient features of this method include the earth-abundant metal catalyst, excellent regioselectivity and good functional group tolerance. Notably, even congested allyl substrates can also be applied to this protocol, thus allowing for the rapid preparation of a series of valuable 1,5-dienes. This journal is

Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and beyond

A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers and external oxidants, allows for efficient and highly regio- and stereoselective synthesis of a broad range of allylic amines from readily available 1,3-dienes, alkyl iodides, and amines. Employment of O- and C-nucleophiles toward oxyalkylation and dialkylation products was also demonstrated. A putative π-allyl palladium radical-polar crossover path is proposed as a key event in this three-component coupling process. The utility of this protocol is highlighted by its application for derivatization of several amine-containing drugs.

Cu-Catalyzed highly regioselective 1,2-hydrocarboxylation of 1,3-dienes with CO2

A practical copper-catalyzed highly regioselective 1,2-hydrocarboxylation of terminal 1,3-diene with carbon dioxide has been developed. Under mild reaction conditions, this chemistry afforded 2-benzyl-β,γ-unsaturated acid derivatives as products, which are a kind of important unit for bio-active molecules and versatile precursors for organic synthesis, with good functional group tolerance. The key intermediate in this transformation is illustrated by control experiments.

Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles

Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.

Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst

We report a method for the catalytic, enantioselective intermolecular addition of aliphatic amines to acyclic 1,3-dienes. In most cases, reactions proceed efficiently at or below room temperature in the presence of 5 mol % of a Pd catalyst bearing a PHOX ligand, generating allylic amines in up to 97:3 er. The presence of an electron-deficient phosphine within the ligand not only leads to a more active catalyst but also is critical for achieving high site selectivity in the transformation.

Enantioselective Aminomethylamination of Conjugated Dienes with Aminals Enabled by Chiral Palladium Complex-Catalyzed C-N Bond Activation

A novel highly enantioselective aminomethylamination of conjugated dienes with aminals catalyzed by a chiral palladium complex ligated with BINOL-derived chiral diphosphinite has been successfully developed. This reaction proceeds via a Pd-catalyzed cascade C-N bond activation, aminomethylation, and asymmetric allylic amination reaction under mild reaction conditions, providing a unique and efficient strategy for the synthesis of enantiomerically pure allylic 1,3-diamines.

A highly selective synthesis of 1-substituted (E)-buta-1,3-dienes with 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane as building block

Highly selective synthesis of 1-substituted (E)-buta-1,3-dienes via palladium-catalyzed Suzuki-Miyaura cross-coupling of (E)-alkenyl iodides with 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (1) is reported. The vinylboronate pinacol ester (1) acts as a vinyl building block to show high chemoselectivity for the Suzuki-Miyaura pathway versus Heck coupling in the presence of biphasic conditions (Pd(PPh3)4, aqueous K 2CO3, toluene and ethanol). Copyright

Titanium-catalyzed intermolecular hydroaminoalkylation of conjugated dienes

Ti me kangaroo down: Conjugated dienes undergo intermolecular hydroaminoalkylation in the presence of Ti catalyst [Ind2TiMe 2] (Ind=η5-indenyl). This new reaction offers a highly atom-efficient approach to homoallylic amines from 1,3-butadienes. Copyright

Stereoselective synthesis of dienes from N-allylhydrazones

(Chemical Equation Presented) A new method for the stereoselective synthesis of dienes from aldehydes and N-allylhydrazine derivatives has been developed. High levels of (E)-stereoselectivity are obtained for a variety of substrates. Addition of a dienoph