7515-42-6

Upstream product

• 100-42-5 styrene 
• 108-05-4 vinyl acetate 
• 16133-83-8 tetrahydro-2-phenylfuran 
• 108-24-7 acetic anhydride 
• 139313-42-1 1,4-diacetoxy-1-phenylbutane 
• 762-72-1 allyl-trimethyl-silane 
• 937-58-6 (3E)-4-phenyl-3-buten-1-ol 
• 75-36-5 acetyl chloride 
• 127-19-5 N,N-dimethyl acetamide 
• 1007-03-0 1-phenyl-1-cyclopropylmethanol 
• 1576-84-7 1-acetoxy-3-butene 

Downstream Products

• 937-58-6 (3E)-4-phenyl-3-buten-1-ol 
• 24104-21-0 acetic acid 4,4-diphenyl-but-3-enyl ester 

Relevant academic research and scientific papers

CuBr2-catalyzed ring opening/formylation reaction of cyclopropyl carbinols with DMF to synthesize formate esters

An unprecedented protocol for the synthesis of formate esters has been developed by employing N,N-dimethylformamide (DMF) as both the source of CHO and solvent. This reaction undergoes ring opening of the cyclopropyl carbinols and in situ formation of homoallylic alcohols, which reacts with DMF to give the desired products. The substrate cyclopropyl carbinols with different groups participate smoothly in this process and the desired products are obtained in moderate to good yields.

Hypervalent iodine initiated intramolecular alkene dimerisation: A stereodivergent entry to cyclobutanes

The emergence of new methods for the stereoselective synthesis of strained carbocycles is a challenging but worthwhile endeavour. Cyclobutanes, in particular, have attracted the attention of both medicinal chemists and material scientists for their unique properties. Herein, we present a new method that allows access to highly functionalized cyclobutanes with complementary all-trans and trans-cis-trans relative stereochemistry, that could not be accessed before. This approach consists of an intramolecular dimerisation of non-conjugated dienes using an oxidative single electron transfer (SET) process, and is initiated by catalytic amounts of hypervalent iodine reagents. The potential uses of these cyclobutanes is demonstrated with selective functionalization, including the formation of diols and carboxylic acids.

HFIP Solvent Enables Alcohols to Act as Alkylating Agents in Stereoselective Heterocyclization

A new method for the stereoselective synthesis of highly functionalized oxygen heterocycles using allyl or benzyl alcohols as alkylating agents is presented. The process is efficient and atom economic, generating water as the only stoichiometric byproduct. Substoichiometric amounts of Ti(OiPr)4 in HFIP solvent are key to this reactivity, and the method tolerates a broad substitution pattern on both the alcohol initiator and homoallylic alcohol substrate. Preliminary mechanistic studies reveal in situ formation of a titanium complex with HFIP which may initiate the cyclization reaction. Further stereoselective functionalization of the products allows access to a diverse range of interesting heterocyclic structures.

Palladium-catalyzed oxidative arylhalogenation of alkenes: Synthetic scope and mechanistic insights

This article describes the development of a Pd-catalyzed reaction for the arylhalogenation (halogen = Cl or Br) of diverse α-olefins by oxidatively intercepting Mizoroki-Heck intermediates. These transformations afford synthetically useful 1,2- and 1,1-arylhalogenated products in good yields with good to excellent selectivities that can be modulated by changing the nature of the halogenating reagent and/or the reaction conditions. The selectivity of these reactions can be rationally tuned by (i) controlling the relative rates of oxidative functionalization versus β-hydride elimination from equilibrating PdII-alkyl species and (ii) stabilization of organometallic PdII intermediates through the formation of π-benzyl adducts. These arylhalogenations exhibit modest to excellent levels of stereoselectivity, and the key carbon-halogen bond-forming step proceeds with predominant retention of stereochemistry at carbon.

InBr3-Catalyzed Deoxygenative Allylation of Benzylic and Allylic Alcohols and Acetates with Allyltrimethylsilane

Deoxygenative allylations of benzylic and allylic alcohols and acetates with allyltrimethylsilane in the presence of a catalytic amount of InBr3 (5 mol percent) were successfully achieved in high yields.