74688-68-9

Upstream product

• 928-95-0 (E)-2-Hexen-1-ol 
• 100-52-7 benzaldehyde 
• 592-41-6 1-hexene 
• 4798-44-1 1-hexene-3-ol 
• 928-94-9 (Z)-2-hexen-1-ol 

Relevant academic research and scientific papers

Catalytic Allylation of Aldehydes Using Unactivated Alkenes

Simple feedstock organic molecules, especially alkenes, are attractive starting materials in organic synthesis because of their wide availability. Direct utilization of such bulk, inert organic molecules for practical and selective chemical reactions, however, remains limited. Herein, we developed a ternary hybrid catalyst system comprising a photoredox catalyst, a hydrogen-atom-transfer catalyst, and a chromium complex catalyst, enabling catalytic allylation of aldehydes with simple alkenes, including feedstock lower alkenes. The reaction proceeded under visible-light irradiation at room temperature and with high functional group tolerance. The reaction was extended to an asymmetric variant by employing a chiral chromium complex catalyst.

Palladium-Catalyzed Oxidative Borylation of Allylic C-H Bonds in Alkenes

This communication describes an efficient palladium pincer complex-catalyzed allylic C-H borylation of alkenes. The transformation exhibits high regio- and stereoselectivity with a variety of linear alkenes. A synthetically useful feature of this allylic C-H borylation method is that all allyl-Bpin products can be isolated in usually high yields. Preliminary mechanistic studies indicate that this C-H borylation reaction proceeds via Pd(IV) pincer complex intermediates.

A convenient one pot allylation of aldehydes with allylic halides prepared in situ from allylic alcohols in the presence of metallic bismuth

The allylation of carbonyl compounds is one of the most fundamental C-C bond forming reactions in organic synthesis. Numerous efficient techniques using allylic organometallics derived from a number of metallic elements have been reported, e.g., the Grign

syn-Diastereoselective carbonyl allylation by 1- or 3-substituted prop-2-en-1-ols with tin(II) iodide and tetrabutylammonium iodide

1-Substituted or 3-substituted prop-2-en-1-ols cause syn-diastereoselective carbonyl allylation with tin(II) iodide and tetrabutylammonium iodide via the formation of 3-substituted prop-2-enylpolyiodotins to produce syn-1,2-disubstituted but-3-en-1-ols.

Palladium-catalyzed carbonyl allylation by allylic alcohols with SnCl2

Allylic alcohols can be applied to carbonyl allylation via the formation of π-allylpalladium complexes, using palladium as catalyst and SnCl2 as a reducing agent. This reaction has chemoselectivity: The reactivity order of allylating agents is allylic carbonate > allylic alcohol > allylic acetate, and that of carbonyl compounds is aldehyde > ketone. High regioselcction was observed in polar solvents such as DMF, DMI, and DMSO; carbonyl compounds apparently attacked the more substituted allylic position of π-allylpalladium complexes to afford only one regioisomer. Diastereocontrol in the carbonyl allylation of aromatic aldehydes by (E)-2-butenol was achieved by the choice of polar solvents; use of DMSO at 25 °C led to syn selection, while anti selection was found at -10 °C in THF. The addition of H2O in any solvent accelerated the carbonyl allylation and enhanced both regioselectivity and the diastereoselectivity. Anti selection in DMF, DMI, and THF-H2O can be explained by the chair form of the six-membered cyclic transition state, while syn selection in DMSO allows us to propose an acyclic antiperiplanar transition state. An NMR spectroscope investigation demonstrated that the actual allylating agent in dry medium was allyltrichlorotin: 1H, 13C, and 119Sn NMR spectra of the reaction of allyl alcohol with PdCl2(PhCN)2-SnCl2 in DMF-d7. corresponded to those of the reaction of allyl chloride with PdCl2(PhCN)2-SnCl2 in DMF-d7.