Photocatalytic Hydroalkylation of Trifluoromethyl Alkenes with Gaseous Alkanes in Flow

Abstract The conversion of light alkanes into value-added products is becoming a field of high interest within the scientific community, as it avoids the use of prefunctionalized alkylating agents. However, the gaseous nature of these reagents, along with their intrinsic inertness due to their high bond-dissociation energies (99–105 kcal·mol–1), have rendered traditional strategies ineffective or lacking in selectivity. The use of flow-chemistry technology has made a tremendous impact in this field, improving the efficiency of multiphasic processes through improved mass transfer and larger interfacial areas. In this work, we report a new flow-chemistry platform for the photocatalytic hydroalkylation of trifluoromethyl alkenes with both isobutane and n-butane. The methodology provides an efficient alternative for the rapid construction of trifluoromethyl alkanes, which are well-known and important bioisosteres of several functional groups.

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Publication Details

Journal
Synlett
Published
2025-05-08
DOI
https://doi.org/10.1055/a-2603-8442
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Photocatalytic Hydroalkylation of Trifluoromethyl Alkenes with Gaseous Alkanes in Flow

Martín Fañanás‐Mastral
Synlett
Fluorine in Organic Chemistry
article

Photocatalytic Hydroalkylation of Trifluoromethyl Alkenes with Gaseous Alkanes in Flow

Martín Fañanás‐Mastral
article en

Abstract

Abstract The conversion of light alkanes into value-added products is becoming a field of high interest within the scientific community, as it avoids the use of prefunctionalized alkylating agents. However, the gaseous nature of these reagents, along with their intrinsic inertness due to their high bond-dissociation energies (99–105 kcal·mol–1), have rendered traditional strategies ineffective or lacking in selectivity. The use of flow-chemistry technology has made a tremendous impact in this field, improving the efficiency of multiphasic processes through improved mass transfer and larger interfacial areas. In this work, we report a new flow-chemistry platform for the photocatalytic hydroalkylation of trifluoromethyl alkenes with both isobutane and n-butane. The methodology provides an efficient alternative for the rapid construction of trifluoromethyl alkanes, which are well-known and important bioisosteres of several functional groups.

SynlettVol. 36(12)
Universidade de Santiago de Compostela (ES), Center for Research in Molecular Medicine and Chronic Diseases (ES)
Consellería de Cultura, Educación e Ordenación Universitaria, Xunta de Galicia, European Regional Development Fund, Agencia Estatal de Investigación
Openalex Percentile: Top 93%
Fluorine in Organic Chemistry
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