190182-16-2

Upstream product

• 98-80-6 phenylboronic acid 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 5661-50-7 N-(phenoxy)acetamide 
• 64908-64-1 2-phenoxyisoindol-1,3-dione 
• 4846-21-3 O-phenylhydroxylamine 
• 5256-79-1 octaphenylsilsesquioxane 
• 104-87-0 4-methyl-benzaldehyde 
• 533-58-4 2-Iodophenol 
• 589-18-4 4-Methylbenzyl alcohol 
• 104-81-4 4-Methylbenzyl bromide 

Downstream Products

• 25664-48-6 2-p-tolyl-benzofuran 

Relevant academic research and scientific papers

A chiral phosphorus alkene ligand, synthetic method and the application of the asymmetric reaction in (by machine translation)

The invention relates to a chiral phosphorus alkene ligand, a synthesis method and application thereof in asymmetric reaction. Specifically, the invention discloses a chiral phosphorus alkene compound, which has a structural formula shown as formula I or formula II in the specification, wherein R, R, R, R, R, R, R, R and R are defined in the specification. The chiral phosphorus alkene compound can be prepared from chiral 2, 2'-binaphthol or its derivative as the starting material through two to four steps of reaction by means of four methods. The chiral phosphorus alkene compound can be used as a chiral ligand in asymmetric addition reaction of rhodium catalyzed boric acid and prochiral C=X (X=C, O, N) double bond, and can achieve good yield and enantioselectivity.

8,10,12 as nanoreactors for non-enzymatic introduction of: Ortho, meta or para -hydroxyl groups to aromatic molecules

Traditional electrophilic bromination follows long established "rules": electron-withdrawing substituents cause bromination selective for meta positions, whereas electron-donating substituents favor ortho and para bromination. In contrast, in the [PhSiO1.5]8,10,12 silsesquioxanes, the cages act as bulky, electron withdrawing groups equivalent to CF3; yet bromination under mild conditions, without a catalyst, greatly favors ortho substitution. Surprisingly, ICl iodination without a catalyst favors (>90%) para substitution [p-IC6H4SiO1.5]8,10,12. Finally, nitration and Friedel-Crafts acylation and sulfonylation are highly meta selective, >80%. In principle, the two halogenation formats coupled with the traditional electrophilic reactions provide selective functionalization at each position on the aromatic ring. Furthermore, halogenation serves as a starting point for the synthesis of two structural isomers of practical utility, i.e. in drug prospecting. The o-bromo and p-iodo compounds are easily modified by catalytic cross-coupling to append diverse functional groups. Thereafter, F-/H2O2 treatment cleaves the Si-C bonds replacing Si with OH. This represents a rare opportunity to introduce hydroxyl groups to aromatic rings, a process not easily accomplished using traditional organic synthesis methods. The as-produced phenol provides additional opportunities for modification. Each cage can be considered a nanoreactor generating 8-12 product molecules. Examples given include syntheses of 4,2′-R,OH-stilbenes and 4,4′-R,OH-stilbenes (R = Me, CN). Unoptimized cleavage of the Br/I derivatives yields 55-85% phenol. Unoptimized cleavage of the stilbene derivatives yields 35-40% (3-5 equivalents of phenol) in the preliminary studies presented here. In contrast, meta R-phenol yields are 80% (7-10 mol per cage).

One-Step Synthesis of Substituted Benzofurans from ortho- Alkenylphenols via Palladium-Catalyzed C=H Functionalization

A dehydrogenative oxygenation of C(sp2)=H bonds with intramolecular phenolic hydroxy groups has been developed, which provides a straightforward and concise access to structurally diversely benzofurans from ortho-alkenylphenols. The reaction is catalyzed by palladium on carbon (Pd/C) without any oxidants and sacrificing hydrogen acceptors.

Rhodium(III)-catalyzed C-H olefination for the Synthesis of ortho-alkenyl phenols using an oxidizing directing group

By using an oxidizing directing group, a mild, efficient Rh(III) catalyzed C-H olefination reaction between N-phenoxyacetamides and alkenes was developed. This reaction provided a straightforward way for the synthesis of ortho-alkenyl phenols, and the directing group is traceless in the product.