1483-60-9

Usage

InChI:InChI=1/C12H18/c1-5-10(3)12-7-6-9(2)8-11(12)4/h6-8,10H,5H2,1-4H3

Upstream product

• 108-38-3 m-xylene 
• 78-92-2 iso-butanol 
• 715-11-7 2-tosyloxybutane 
• 126-73-8 phosphoric acid tributyl ester 
• 104-15-4 toluene-4-sulfonic acid 
• 2528-45-2 Tri-sec-butyl phosphate 
• 88496-88-2 1-methylpropylboronic acid 
• 95-66-9 2,4-dimethylchlorobenzene 
• 583-70-0 1-bromo-2,4-dimethylbenzene 
• 142509-27-1 5-(1-methylpropyl)-1-aza-5-stannabicyclo[3.3.3]undecane 
• 598-30-1 sec.-butyllithium 
• 87241-53-0 2,4-dimethylphenyl nonaflate 
• 87241-52-9 2,4-dimethylphenyl trifluoromethanesulfonate 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 98-19-1 5-tert-Butyl-m-xylene 
• 939-37-7 1-(sec-butyl)-3,5-dimethylbenzene 
• 39568-70-2 1,2,3,5-tetrabromo-4,6-dimethyl-benzene 

Relevant academic research and scientific papers

Stereospecific Pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides

We report the development of a Pd-catalyzed process for the stereospecific cross-coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides. This process tolerates the use of secondary alkylboronic acids and secondary alkyltrifluoroborates and occurs without significant isomerization of the alkyl nucelophile. Optically active secondary alkyltrifluoroborate reagents undergo cross-coupling reactions with stereospecific inversion of configuration using this method.

Stereoretentive Pd-catalysed Stille cross-coupling reactions of secondary alkyl azastannatranes and aryl halides

The development of transition metal-catalysed cross-coupling reactions has greatly influenced the manner in which the synthesis of complex organic molecules is approached. A wide variety of methods are now available for the formation of C(sp2)-C(sp2) bonds, and more recent work has focused on the use of C(sp3) electrophiles and nucleophiles. The use of secondary and tertiary alkyl nucleophiles in cross-coupling reactions remains a challenge because of the propensity of these alkyl groups to isomerize under the reaction conditions. Here, we report the development of a general Pd-catalysed process for the stereoretentive cross-coupling of secondary alkyl azastannatrane nucleophiles with aryl chlorides, bromides, iodides and triflates. Coupling partners with a wide range of electronic characteristics are well tolerated. The reaction occurs with minimal isomerization of the secondary alkyltin nucleophile, and with retention of absolute configuration. This process constitutes the first general method to use secondary alkyltin reagents in cross-coupling reactions.

REACTION OF PHOSPHORUS OXYACID ESTERS WITH p-TOLUENESULFONIC ACID

The reaction of primary alkyl esters of phosphorus oxyacids with p-toluenesulfonic acid (TsOH) in refluxing solvents gave the corresponding p-toluenesulfonates (TsOR).We found that the secondary alkyl esters reacted with TsOH at lower temperature (r.t.-40 deg C) to afford TsORs in good yields.It is suggested that sulfonic acids may be useful for the selective dealkylation of mixed esters.Keywords-p-toluenesulfonic acid; p-toluenesulfonate; trialkyl phosphate; trialkyl phosphite; dialkyl phenylphosphonate; transesterification; dealkylation; solvolysis.

SYNTHESIS OF ARENES FROM PHENOLS BY COUPLING OF ARYL TRIFLATES WITH ORGANOCOPPER REAGENTS

Aryl triflates react with higher order mixed cuprates R2Cu(CN)Li2 to produce arenes in good yield.The aryl ring may have either an electron-donating or an electron-withdrawing substituent; the organocuprate may be either primary, secondary, tertiary, aryl, or vinyl.