5751-32-6

Upstream product

• 1014394-68-3 (E)-3-(naphthalen-2-yl)allyl pivalate 
• 143-66-8 sodium tetraphenyl borate 
• 115117-86-7 (2E)-3-(2-naphthyl)prop-2-en-1-yl acetate 
• 66-99-9 β-naphthaldehyde 
• 100-52-7 benzaldehyde 
• 93-08-3 methyl 2-naphthyl ketone 
• 56345-32-5 1-(naphthalen-2-yl)-3-phenylprop-2-en-1-ol 
• 4782-69-8 1-(naphthalen-2-yl)-3-phenylprop-2-en-1-one 
• 76635-88-6 vinyl-2-naphthylcarbinol 
• 111928-10-0 tetraphenylphosphonium trifluoromethanesulfonate 
• 300-57-2 allylbenzene 
• 91-20-3 naphthalene 
• 135-19-3 β-naphthol 
• 61124-61-6 3-phenylpropanal p-tosylhydrazone 

Relevant academic research and scientific papers

Olefination with Sulfonyl Halides and Esters: Scope, Limitations, and Mechanistic Studies of the Hawkins Reaction

Carbanions of alkanesulfonyl halides and esters react with nonenolizable carbonyl compounds to give olefins. Mechanistic studies reveal that initial aldol-type addition of the carbanions is followed by cyclization-fragmentation to alkenes, and the leaving group on the sulfonyl moiety (RSO2X) controls carbanion stability and rate of the olefin formation.

Nickel-Catalyzed Reductive Csp2-Csp3Cross Coupling Using Phosphonium Salts

A nickel-catalyzed reductive cross coupling with phosphonium salts and allylic C(sp3)-O bond electrophiles, which granted direct construction of the C(sp2)-C(sp3) bond, is successfully developed. The protocol features broad substrate scope, high-functional-group tolerance, and heterocycle compatibility. Notably, the much more challenging reductive cross coupling with heterocyclic thiazolylphosphonium salts has also been accomplished for the first time.

S,O-ligand-promoted palladium-catalyzed C–H olefination of arenes with allylic substrates

An efficient catalytic system for the C–H olefination of arenes with different allylic substrates is reported. The catalytic system is based on Pd(OAc)2 and a readily accessible bidentate S,O-ligand. The methodology shows high activity with a wide range of arenes, including bulky and, electron-rich and -poor arenes. The applicability of this catalyst is demonstrated in the late-stage functionalization of the complex molecule O-methylestrone.

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.

A palladium NNC-pincer complex: An efficient catalyst for allylic arylation at parts per billion levels

Allylic arylation of allylic acetates by sodium tetraarylborates in the presence of ppb to ppm (molar) loadings of a palladium NNC-pincer complex catalyst in methanol at 50°C gave the corresponding arylated products in excellent yields. Total turnover numbers of up to 500 000 000 and turnover frequencies of up to 11 250 000 h-1 were achieved.

A vesicular self-assembled amphiphilic palladium NNC-pincer complex-catalyzed allylic arylation of allyl acetates with sodium tetraarylborates in water

Abstract The allylic arylation of various allyl acetates with sodium tetraarylborates proceeded in water in the presence of a vesicular self-assembled amphiphilic palladium NNC-pincer complex to give the corresponding arylated products in high yield, wher

Nickel(0)-catalyzed heck cross-coupling via activation of aryl C-OPiv bonds

Using a Ni(dppf) catalyst generated in situ, Heck cross-coupling of aryl pivalates with a variety of olefin partners has been accomplished. This method represents one of the first examples of a C-C cross-coupling via activation of a strong C-O bond with a

Synthesis of polysubstituted olefins by Pd-catalyzed cross-coupling reaction of tosylhydrazones and aryl nonaflates

Aryl nonaflates are employed as electrophiles in the Pd-catalyzed cross-coupling with tosylhydrazones affording di-, tri-, and tetrasubstituted olefins. Fine tunning of the reaction conditions are required to accomplish the coupling successfully, includin

Enantioselective iridium-catalyzed allylic arylation

We describe herein the development of the first iridium-catalyzed allylic substitution using arylzinc nucleophiles. High enantioselectivities were obtained from the reactions, which used commercially available Grignard reagents as the starting materials. This methodology was also shown to be compatible with halogen/metal exchange reactions. Its synthetic potential is demonstrated by its application towards the formal synthesis of (+)-sertraline.

Development of biisoquinoline-based chiral diaminocarbene ligands: Enantioselective SN2′ allylic alkylation catalyzed by copper-carbene complexes

Chiral biisoquinoline-based diaminocarbene ligands (BIQ) were designed to create a chiral environment extended toward the metal center, which was confirmed by an X-ray structure. The concise ligand synthesis is highlighted by a modified Bischler-Napieralski cyclization of bisamides prepared from readily available chiral phenethylamines, and allows easy variation of the stereodifferentiating groups. The cyclohexyl-BIQ-copper complex is an efficient catalyst for enantioselective SN2′ allylic alkylation with Grignard reagents showing SN2′ regioselectivity higher than 5:1 and enantioselectivity in the range of 68-77% ee.