Site-Selective Palladium(II)-Catalyzed Methylene C(sp3)-H Diarylation of a Tropane Scaffold

Mayssa Zayene; Franck Le Bideau; Pascal Retailleau; Hichem Ben Jannet; Mouad Alami; Anis Romdhane; Samir Messaoudi

doi:10.1021/acs.joc.2c02081

Site-Selective Palladium(II)-Catalyzed Methylene C(sp³)-H Diarylation of a Tropane Scaffold

Mayssa Zayene
, Franck Le Bideau
, Pascal Retailleau
, Hichem Ben Jannet
, Mouad Alami
, Anis Romdhane
, Samir Messaoudi

Université Paris-Sud
Laboratory of Heterocyclic Chemistry
Faculté des Sciences de Monastir
Institut de Chimie des Substances Naturelles

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

A series of 2,4-di-arylated tropane derivatives was synthesized through a site-selective palladium-catalyzed β-C(sp3)-H di-arylation process. This type of structure has been scarcely reported in literature. They nevertheless represent an interesting class of biologically relevant molecules as illustrated by the observed activity at the micromolecular level of eight derivatives toward human colorectal cancer cell line HCT116.

Original language	English
Pages (from-to)	16399-16409
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	87
Issue number	24
DOIs	https://doi.org/10.1021/acs.joc.2c02081
Publication status	Published - 16 Dec 2022
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Access to Document

10.1021/acs.joc.2c02081

Cite this

@article{89ab9651b5d444bdb1bf3494fadcfcf5,

title = "Site-Selective Palladium(II)-Catalyzed Methylene C(sp3)-H Diarylation of a Tropane Scaffold",

abstract = "A series of 2,4-di-arylated tropane derivatives was synthesized through a site-selective palladium-catalyzed β-C(sp3)-H di-arylation process. This type of structure has been scarcely reported in literature. They nevertheless represent an interesting class of biologically relevant molecules as illustrated by the observed activity at the micromolecular level of eight derivatives toward human colorectal cancer cell line HCT116.",

author = "Mayssa Zayene and \{Le Bideau\}, Franck and Pascal Retailleau and Jannet, \{Hichem Ben\} and Mouad Alami and Anis Romdhane and Samir Messaoudi",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

month = dec,

day = "16",

doi = "10.1021/acs.joc.2c02081",

language = "English",

volume = "87",

pages = "16399--16409",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - Site-Selective Palladium(II)-Catalyzed Methylene C(sp3)-H Diarylation of a Tropane Scaffold

AU - Zayene, Mayssa

AU - Le Bideau, Franck

AU - Retailleau, Pascal

AU - Jannet, Hichem Ben

AU - Alami, Mouad

AU - Romdhane, Anis

AU - Messaoudi, Samir

PY - 2022/12/16

Y1 - 2022/12/16

N2 - A series of 2,4-di-arylated tropane derivatives was synthesized through a site-selective palladium-catalyzed β-C(sp3)-H di-arylation process. This type of structure has been scarcely reported in literature. They nevertheless represent an interesting class of biologically relevant molecules as illustrated by the observed activity at the micromolecular level of eight derivatives toward human colorectal cancer cell line HCT116.

AB - A series of 2,4-di-arylated tropane derivatives was synthesized through a site-selective palladium-catalyzed β-C(sp3)-H di-arylation process. This type of structure has been scarcely reported in literature. They nevertheless represent an interesting class of biologically relevant molecules as illustrated by the observed activity at the micromolecular level of eight derivatives toward human colorectal cancer cell line HCT116.

U2 - 10.1021/acs.joc.2c02081

DO - 10.1021/acs.joc.2c02081

M3 - Article

AN - SCOPUS:85143691798

SN - 0022-3263

VL - 87

SP - 16399

EP - 16409

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24