2114-41-2

Upstream product

• 134046-86-9 (E)-1-cyclohexyl-1-trimethylsilyl-1-propene 
• 88533-71-5 (R*,S*)-2-Diphenylphosphinoyl-1-cyclohexylpropan-1-ol 
• 110-82-7 cyclohexane 
• 74-99-7 prop-1-yne 
• 103687-21-4 ((CH₃)3C₆H₂)2BCHLiCH₃ 
• 2043-61-0 cyclohexanecarbaldehyde 
• 1754-88-7 ethylenetriphenylphosphorane 
• 89091-87-2 1-cyclohexyl-2-diphenylphosphinoylpropan-1-one 
• 2114-42-3 allylcyclohexane 
• 88533-71-5 (R*,R*)-2-Diphenylphosphinoyl-1-cyclohexylpropan-1-ol 
• 113686-82-1 dibenzophosphole-ethylide 
• 590-15-8 trans-2-propenyl bromide 
• 915377-98-9 1-cyclohexyl-1-(methyl-diphenyl-silanyl)-propan-2-ol 
• 1568-65-6 bis(cyclohexanyl)borane 

Downstream Products

• 81435-40-7 threo-1-cyclohexyl-2-methyl-4-phenyl-3-butyn-1-ol 
• 164323-45-9 (2S,3R)-2-cyclohexyl-3-methyloxirane 
• 164323-45-9 (2R,3S)-2-cyclohexyl-3-methyloxirane 
• 81435-40-7 erythro-1-cyclohexyl-2-methyl-4-phenyl-3-butyn-1-ol 

Relevant academic research and scientific papers

METHODS OF BORYLATION AND USES THEREOF

The present invention relates, in general terms, to methods of borylation and uses thereof. In particular, the present invention provides a method of borylating an alkene compound by contacting the compound with a boron compound, a Fe pre-catalyst and a protic additive. The borylation occurs at a vicinal (β) position to an electron donating or electron withdrawing moiety of the compound.

Visible-Light Controlled Divergent Catalysis Using a Bench-Stable Cobalt(I) Hydride Complex

While the use of visible light in conjunction with transition metal catalysis offers powerful opportunities to switch between on/-off states of catalytic activity, the next frontier would be the ability to switch the actual function of the catalyst and resulting products. Here we report such an example of multi-dimensional catalysis. Featuring an easily prepared, bench-stable cobalt(I) hydride complex in conjunction with pinacolborane, we can switch the reaction outcome between two widely employed transformations, olefin migration and hydroboration, with visible light as the trigger.

Iron-Catalyzed Tunable and Site-Selective Olefin Transposition

The catalytic isomerization of C-C double bonds is an indispensable chemical transformation used to deliver higher-value analogues and has important utility in the chemical industry. Notwithstanding the advances reported in this field, there is compelling demand for a general catalytic solution that enables precise control of the C═C bond migration position, in both cyclic and acyclic systems, to furnish disubstituted and trisubstituted alkenes. Here, we show that catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound, promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/β-hydride elimination. Through this strategy, regiodivergent access to different products from one substrate can be facilitated, isomeric olefin mixtures commonly found in petroleum-derived feedstock can be transformed to a single alkene product, and unsaturated moieties embedded within linear and heterocyclic biologically active entities can be obtained.

An alternative mechanism for the cobalt-catalyzed isomerization of terminal alkenes to (Z)-2-alkenes

The cobalt-catalyzed selective isomerization of terminal alkenes to the thermodynamically less-stable (Z)-2-alkenes at ambient temperatures takes place by a new mechanism involving the transfer of a hydrogen atom from a Ph2PH ligand to the starting material and the formation of a phosphenium complex, which recycles the Ph2PH complex through a 1,2-H shift.

Double-Bond Isomerization: Highly Reactive Nickel Catalyst Applied in the Synthesis of the Pheromone (9 Z,12 Z)-Tetradeca-9,12-dienyl Acetate

A highly reactive nickel catalyst comprising NiCl2(dppp) or NiCl2(dppe) with zinc powder, ZnI2 and Ph2PH, was applied in the isomerization of terminal alkenes to Z-2-alkenes. The double-bond geometry of the 2-alkene can be controlled via the reaction temperature to yield the 2-Z-alkenes in excellent yields and high Z-selectivities. The formation of other constitutional isomers, such as 3-alkenes, is suppressed on the basis of the proposed mechanism via a 1,2-hydride shift from the metal to the Ph2P ligand. The nickel-catalyzed isomerization reaction was then applied in the synthesis of (9Z,12Z)-tetradeca-9,12-dienyl acetate, a pheromone with a 2Z,5Z-diene subunit.

Palladium-catalyzed asymmetric silaboration of allenes

An enantioselective silaboration of allenes was achieved using an achiral silylborane in the presence of a palladium catalyst bearing a chiral monodentate phosphine ligand. (R)-2-Bis(3,5-dimethylphenyl)phosphino-1,1-binaphthyl gave the highest enantiosele

Highly chemo- and stereoselective Fe-catalyzed alkenylation of organomanganese reagents

Organomanganese chlorides react with alkenyl iodides, bromides and chlorides in the presence of 3% Fe(acac)3. The reaction takes place under very mild conditions (THF-NMP, rt, 1h) to afford the substituted olefin in excellent yields with a high stereo- and chemoselectivity. Thus an unprotected keto alkenyl chloride selectively gives the corresponding keto olefin. From a preparative point of view, this procedure is the first real alternative to the Pd- and Ni-cross coupling reaction used until now.

Hindered organoboron groups in organic chemistry. 25. The condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions to give alkenes

In the presence of protic acids the condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions results in alkenes. In the presence of strong acids such as HCl or CF3SO3H, the products contain > 90% of E-alkenes in all cases tried. When acetic acid is used, the Z-alkenes may result predominantly, particularly in the cases of R(S)CHO and R(t)CHO.

A Bridged Tetrahydrophosphole Ylide Derived from 9-Phenylphosphabicyclononane: A Reagent for E-Selective Wittig Reactions

The bicyclic ylide 4 reacts with aldehydes to afford the E-alkenes.Selectivity is 94 - 6percent E for unbranched aldehydes, but the selectivity decreases with increasing α-branching.Ylide 4 is the first E-selective, nonstabilized ylide that allows efficient utilization of the P-alkyl substituent.

Stereoselectivity of the Thermally Initiated Free-Radical Chain Addition of Cyclohexane to 1-Alkynes

Alkanes can be added to alkynes in a thermally initiated free-radical chain reaction ("ane reaction").The addition of cyclohexane to 1-alkynes 1a-l yields a mixture of (Z)- and (E)-2-cyclohexyl-1-alkenes 3a-l.An essential step in this reaction is the addi