Development of Transition-Metal-Free Lewis Acid-Initiated Double Arylation of Aldehyde: A Facile Approach Towards the Total Synthesis of Anti-Breast-Cancer Agent.
Chemistry
; 28(14): e202104545, 2022 Mar 07.
Article
in En
| MEDLINE
| ID: mdl-35060647
ABSTRACT
This work describes a mild and robust double hydroarylation strategy for the synthesis of symmetrical /unsymmetrical diaryl- and triarylmethanes in excellent yields using Lambert salt (0.2-1.0â
mol%). Despite the anticipated challenges associated with controlling selective product formation, unsymmetrical diaryl- and triarylmethanes products are obtained unprecedentedly. A highly efficient gram scale reaction has also been reported (TON for symmetrical product=475 and for unsymmetrical product=390). The synthetic utility of the methodology is demonstrated by the preparation of several unexplored diaryl- and triarylmethane-based biologically relevant molecules, such as arundine, vibrindole A, turbomycin B, and certain anti-inflammatory agents. A total synthesis of an anti-breast-cancer agent is also demonstrated. Control experiments, Hammett analysis, HRMS and GC-MS studies reveal the reaction intermediates and reaction mechanism.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Transition Elements
/
Neoplasms
Language:
En
Journal:
Chemistry
Journal subject:
QUIMICA
Year:
2022
Document type:
Article
Affiliation country:
India