One-pot hydroformylation/O-acylation of propenylbenzenes for the synthesis of polyfunctionalized fragrances

Delolo, Fábio G.; Vieira, Gabriel Matos; Avendaño-Villarreal, Jesus A.; Santos, Eduardo N. dos; Gusevskaya, Elena V.

doi:10.1016/j.cattod.2020.04.053

Cited by 9 publications

(2 citation statements)

References 25 publications

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“…[26,27] For several years we have been focusing our efforts on the catalytic valorization of natural compounds; [28,29] in particular, through the hydroformylation-based tandem processes. [30][31][32][33][34][35][36][37] In the present work, we describe the HAM reaction of a series of allylic and homoallylic terpenic alcohols with secondary amines aiming to obtain complex amines of pharmaceutical relevance. The hydroformylation of allylic and homoallylic alcohols usually results directly in cyclic hemiacetals due to the fast cyclization of primarily formed hydroxyaldehydes, [38] which could present an obstacle for the HAM sequence.…”

Section: Introductionmentioning

confidence: 99%

“…For several years we have been focusing our efforts on the catalytic valorization of natural compounds; [28,29] in particular, through the hydroformylation‐based tandem processes [30–37] . In the present work, we describe the HAM reaction of a series of allylic and homoallylic terpenic alcohols with secondary amines aiming to obtain complex amines of pharmaceutical relevance.…”

Section: Introductionmentioning

confidence: 99%

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Hydroaminomethylation of Natural Allylic and Homoallylic Alcohols: A Ligand‐Controlled Route to New Amines

et al. 2022

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Hydroaminomethylation (HAM) is a tandem catalytic process that allows accessing amines from olefin scaffolds and is perfectly aligned with green chemistry precepts. In this work, HAM was applied to the natural hydroxyolefins: isoprenol, linalool, nerolidol, and isopulegol. Employing 4‐methylpiperidine, morpholine, and 1,2,3,4‐tetrahydroisoquinoline as counterparts, several new, structurally complex amines were prepared from biorenewable, low‐cost substrates, opening a path to exploit this structure diversity in biological activity. By the appropriate choice of rhodium‐based catalytic systems, as well as the reaction conditions, the necessary fine tuning for each counterpart was achieved. The unpromoted rhodium system leaded mostly to aminoalcohols, while certain phosphorus(III)‐promoted rhodium systems afforded amines containing a tetrahydropyran or a tetrahydrofuran moiety in moderate to high yields.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hydroaminomethylation of Natural Allylic and Homoallylic Alcohols: A Ligand‐Controlled Route to New Amines

et al. 2022

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One‐Pot Reactions in Different Sites: A New Approach in Hydroformylation‐Based Processes

Delolo,

dos Santos,

Gusevskaya

2024

ChemCatChem

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One‐pot synthetic procedures allow multiple chemical transformations circumventing the isolation of intermediates and thus saving time, energy and feedstocks. Within the scope of one‐pot processes, cascade, domino, or tandem procedures are even more efficient, as multiple reactions can occur in parallel. Hydroformylation is an industrially relevant reaction particularly suitable for this kind of methodology, as the primary products (aldehydes) are usually converted into compounds containing other functionalities. In addition to examples of transformations of the substrate before the hydroformylation step or the transformation of the aldehyde into other functionalities, we highlight a novel approach, in which an additional functionalization takes place in a remote site of the substrate molecule, along with the hydroformylation of the carbon‐carbon double bond.

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Production of diacetates from propenylphenols: A one-pot two-step approach involving hydroformylation/hydrogenation/O-acylation

Dias,

Delolo,

Avendaño-Villarreal

et al. 2023

Applied Catalysis A: General

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One-pot hydroformylation/O-acylation of propenylbenzenes for the synthesis of polyfunctionalized fragrances

Cited by 9 publications

References 25 publications

Hydroaminomethylation of Natural Allylic and Homoallylic Alcohols: A Ligand‐Controlled Route to New Amines

Hydroaminomethylation of Natural Allylic and Homoallylic Alcohols: A Ligand‐Controlled Route to New Amines

One‐Pot Reactions in Different Sites: A New Approach in Hydroformylation‐Based Processes

Production of diacetates from propenylphenols: A one-pot two-step approach involving hydroformylation/hydrogenation/O-acylation

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