52809-43-5

Upstream product

• 5195-24-4 4,4-dimethyl-1-phenylpentan-3-one 
• 3121-79-7 4,4-dimethyl-1-pentanol 
• 546-67-8 lead(IV) tetraacetate 
• 100-44-7 benzyl chloride 
• 630-19-3 pivalaldehyde 
• 103-63-9 1-phenyl-2-bromoethane 
• 71-43-2 benzene 
• 594-19-4 tert.-butyl lithium 
• 134414-86-1 (3,3-dibromopropyl)benzene 
• 213380-00-8 C₂₂H₃₂N₂O₂SSi 
• 132381-67-0 C₂₂H₂₀OS 
• 141694-57-7 Trifluoro-methanesulfonic acid 3-phenyl-1-trifluoromethanesulfonyloxy-propyl ester 
• 104-53-0 3-phenyl-propionaldehyde 
• 75-97-8 3,3-dimethyl-butan-2-one 

Relevant academic research and scientific papers

Synthesis of quinolinyl-based pincer copper(ii) complexes: an efficient catalyst system for Kumada coupling of alkyl chlorides and bromides with alkyl Grignard reagents

Quinolinamide-based pincer copper(ii) complexes, κN,κN,κN-{C9H6N-(μ-N)-C(O)CH2NEt2}CuX [(QNNNEt2)CuX (X = Cl, 2; X = Br, 3; X = OAc, 4)], were synthesized by the reaction of ligand (QNNNEt2)-H (1) with CuX2 (X = Cl, Br or OAc) in the presence of Et3N. The reaction of (QNNNEt2)-H with CuX (X = Cl, Br or OAc) also afforded the Cu(ii) complexes 2, 3 and 4, respectively, instead of the expected Cu(i) pincer complexes. The formation of Cu(ii) complexes from Cu(i) precursors most likely occurred via the disproportionation reaction of Cu(i) into Cu(0) and Cu(ii). A cationic complex [(QNNNEt2)Cu(CH3CN)]OTf (5) was synthesized by the treatment of neutral complex 2 with AgOTf. On the other hand, the reaction of (QNNNEt2)-H (1) with [Cu(MeCN)4]ClO4 produced cationic Cu(i) complex, [(QNN(H)NEt2)Cu(CH3CN)]ClO4 (6), in good yield. All complexes 2-5 were characterized by elemental analysis and HRMS measurements. Furthermore, the molecular structures of 2, 3 and 4 were elucidated by X-ray crystallography. Complex 4 crystallizes in a dimeric and catemeric pattern. The cationic complex 5 was found to be an efficient catalyst for the Kumada coupling reaction of diverse nonactivated alkyl chlorides and bromides with alkyl magnesium chloride under mild reaction conditions.

Catalytic synthesis of n-alkyl arenes through alkyl group cross-metathesis

n-Alkyl arenes were prepared in a one-pot tandem dehydrogenation/olefin metathesis/hydrogenation sequence directly from alkanes and ethylbenzene. Excellent selectivity was observed when (tBuPCP)IrH2 was paired with tungsten monoaryloxide pyrrolide complexes such as W(NAr)(C 3H6)(pyr)(OHIPT) (1a) [Ar = 2,6-i-Pr2C 6H3; pyr = pyrrolide; OHIPT = 2,6-(2,4,6-i-Pr 3C6H2)2C6H3O]. Complex 1a was also especially active in n-octane self-metathesis, providing the highest product concentrations reported to date. The thermal stability of selected olefin metathesis catalysts allowed elevated temperatures and extended reaction times to be employed.

Copper-catalyzed cross-coupling of nonactivated secondary alkyl halides and tosylates with secondary alkyl grignard reagents

Practical catalytic cross-coupling of secondary alkyl electrophiles with secondary alkyl nucleophiles under Cu catalysis has been realized. The use of TMEDA and LiOMe is critical for the success of the reaction. This cross-coupling reaction occurs via an SN2 mechanism with inversion of configuration and therefore provides a general approach for the stereocontrolled formation of C-C bonds between two tertiary carbons from chiral secondary alcohols.

Geminal dialkylation, alkylative reduction and olefination of aliphatic aldehydes. Reaction of gem-bistriflates with higher order dialkylcyanocuprates

gem-Dialkylation or alkylative reduction of α-unbranched aliphatic aldehydes 1 is advantageously achieved by reaction of the corresponding gem-bistriflates 2 with di-n-alkylcyanocuprates or di-sec- and di-tert-alkylcyanocuprates respectively. The reaction of α-branched gem-bistriflates 2 with dialkylcyanocuprates in the presence of boron trifluoride affords the olefins 6 in good yield.

Geminal Dialkylation and Alkylative Reduction of Alyphatic Aldehydes.

gem-Dialkylation or alkylative reduction of α-unbranched aliphatic aldehydes is easily carried out by replacing the carbonyl oxygen with the gem-dihalide functionality followed by substitution of each halogen (bromine or iodine) by two n-alkyl groups or one sec- or tert-alkyl group and one hydrogen atom using higher-order dialkyl-lithium cyanocuprates.

Radical Substitution on the Sulphur of Thioester Group

Intermolecular reaction of an organo-radical with thioester gives the sulphide, which is formed by the sulphur centred substitution of acyl groups with a nucleophilic organo-radical, but no displacement of S-alkyl groups with the organo-radical takes place.