10468-83-4

Upstream product

• 124-38-9 carbon dioxide 
• 81770-12-9 1-p-biphenylyl-2-chloro-2-methylpropane 
• 81770-11-8 2-p-biphenylyl-1-chloro-2-methylpropane 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 677-22-5 tert-butylmagnesium chloride 

Downstream Products

• 81770-25-4 1-isobutyl-4-cyclohexylbenzene 
• 6976-20-1 1-([1,1′-biphenyl]-4-yl)-2-methylpropan-1-one 

Relevant academic research and scientific papers

Ligand-free nickel-catalyzed Kumada couplings of aryl bromides with tert-butyl Grignard reagents

A ligand-free nickel-catalyzed Kumada cross-coupling of aryl bromides and tert-butyl Grignard reagents led to the formation of a series of tert-butyl aryls in moderate to good yields, excellent tBu/iBu ratios, and good functional group compatibility. A radical coupling process is indicated and a mechanism with a Ni(I)-Ni(III) catalytic cycle is proposed.

Benzo polyaza and phosphole oxygen ligand and complex containing same, preparation method and application

The invention discloses a benzo polyaza and phosphole oxygen ligand and a complex containing same, a preparation method and application. The invention provides a benzo polyaza and phosphole oxygen ligand as shown in formula I and a complex containing same. A complex of the benzo polyaza and phosphole oxygen ligand and a transition metal halide enables direct coupling of carbon-carbon bonds betweenbig steric hindrance alkyl and aryl; the reaction conditions are gentle; the catalyzing efficiency is high; the coupling reaction process of the carbon-carbon bonds between big steric hindrance alkyland aryl can be extremely simplified; the practicability is high; the reaction cost can be obviously decreased, and the reaction period is reduced; the complex is free from other side products without being required in the catalyzing process. The formula refers to the description.

Nickel-catalyzed cross-coupling of aryl bromides with tertiary grignard reagents utilizing donor-functionalized N-heterocyclic carbenes (NHCs)

Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis, allowing the efficient construction of complex structures from simpler, readily available building blocks.Many applications in large and small-scale synthesis can be found in different areas such as agrochemicals, pharmaceuticals and supramolecular chemistry. Whereas the coupling of sp2-hybridized carbon atoms in either reaction partner is well established, the use of CACHTUNGTRENUNG(sp3)-hybridized substrates presents some challenges. Catalytic cross-coupling of sterically hindered tertiary alkyl substrates is especially difficult, generally resulting in low yields, and thus, only few reports exist.[27] A big challenge in this field is not only to get the required level of reactivity, but also to overcome competing pathways like β-hydride elimination, hydrodehalogenation or isomerization

Carbanions. 21. Reactions of 2- and 3-p-Biphenylylalkyl Chlorides with Alkali Metals. Preparation of Labile Spiro Anions

The present work was undertaken to see if (3-p-biphenylylpropyl)- and (2-p-biphenylethyl)cesium cyclize like (4-p-biphenylbutyl)cesium to stable spiro anions.Reaction of 1-p-biphenylyl-3-chloropropane (5) with Cs-K-Na alloy in THF at -75 deg C gave, under the optimum conditions found, 36percent of 7-phenylspironona-6,5-dien-5-yl anion (8) besides 3-p-biphenylylpropyl (7), 1-p-biphenylylpropyl (9), and p-biphenylylmethyl (10) anions, according to the products of carbonation.The spiro anion 8 (Cs+ as the counterion) has a half-life of about 13 min at -75 deg C.Incontrast, 5 reacts with lithium to give predominantly (3-p-biphenylylpropyl)lithium.Reaction of 1-p-biphenylyl-2-chloroethane with Cs-K-Na alloy gave no appreciable spiro anion under conditions which were successful with 5.In the reaction of 1-p-biphenylyl-2-chloro-2-methylpropane (28) with Cs-K-Na alloy the α-gem-dimethyl group accelerates migration of the p-biphenylyl group to give products similar to those from 2-p-biphenylyl-1-chloro-2-methylpropane (24); however, the expected intermediate spiro anion 26 was undetectable by the carbonation technique.With both α- and β-gem-dimethyl groups, 2-p-biphenylyl-3-chloro-2,3-dimethylbutane (41) reacts with Cs-K-Na alloy to give 1,1,2,2-tetramethyl-6-phenylspiroocta-5,7-dien-4-yl anion (43) and 2-p-biphenylyl-1,1,2-trimethylpropyl anion (42) in about a 2:1 ratio according to the results of carbonation.The open anion 42 and the spiro anion 43 appear to be in mobile equilibrium (Cs+ as the counterion) with half-lives of about 22 min in THF at -75 deg C.With lithium as counterion, only the open product (2-p-biphenylyl-1,1,2-trimethylpropyl)lithium (50) was detectable by carbonation.