2026-10-13T12:04:29Z
https://api.figshare.com/v2/oai
oai:figshare.com:article/34028591
2026-09-30T02:06:15Z
category_4
category_19
category_272
category_873
category_39
category_45
portal_63
item_type_6
month_year_09_2026
Chiral Arylthiol-Catalyzed
Asymmetric Hydrodifluoroalkylation
of Alkenes Facilitated by Noncovalent Interaction
Jing Wang (6206297)
Chaoren Shen (1608913)
Guangzhu Wang (10428674)
Ruixin Zhang (48813)
Kaiwu Dong (1602601)
Biochemistry
Pharmacology
Environmental Sciences not elsewhere classified
Chemical Sciences not elsewhere classified
Ecology
Sociology
valuable fluorinated bioisosteres
photodriven enantioselective hydrodifluoroalkylation
medicinally important ch
mechanistic investigation reveals
free energy difference
>- phenyl group
>- dimethyl substituent
>- difluorinated indane
protocol delivers chiral
noncovalent interaction chiral
catalyzed asymmetric hydrodifluoroalkylation
chiral arylthiol
bromodifluoroamides catalyzed
n </
high enantioselectivities
gem </
excellent yields
derived amides
c </
alkenes facilitated
Chiral <i>gem</i>-difluorinated indane scaffolds
are
valuable fluorinated bioisosteres of medicinally important CH<sub>2</sub>-containing indane frameworks. Herein, a photodriven enantioselective
hydrodifluoroalkylation of methyleneindanes with α-bromodifluoroamides
catalyzed by a <i>C</i><sub>2</sub>-symmetric chiral arylthiol
was developed. This protocol delivers chiral <i>gem</i>-difluorinated
indane-derived amides in good to excellent yields with high enantioselectivities.
Mechanistic investigation reveals that the <i>gem</i>-dimethyl
substituent in the substrate is critical to amplify the free energy
difference between diastereomeric HA transition states, while a π–π
interaction between the substrate <i>N</i>-phenyl group
and the arylthiol catalyst benzylic substituent underpins the enantiocontrol.
2026-09-29T00:00:00Z
Text
Journal contribution
10.1021/acs.orglett.6c03878.s001
https://figshare.com/articles/journal_contribution/Chiral_Arylthiol-Catalyzed_Asymmetric_Hydrodifluoroalkylation_of_Alkenes_Facilitated_by_Noncovalent_Interaction/34028591
CC BY-NC 4.0