Two Approaches in the Synthesis of Planar Chiral Azinylferrocenes / Utepova Irina A.,Chupakhin Oleg N.,Serebrennikova Polina O.,Musikhina Alexandra A.,Charushin Valery N. // JOURNAL OF ORGANIC CHEMISTRY. - 2014. - V. 79, l. 18. - P. 8659-8667.

ISSN/EISSN:

0022-3263 / нет данных

Type:

Article

Abstract:

Two synthetic routes to the chiral azinylferrocenes (CAFs) 5 and 15, key intermediates for the synthesis of new enantiomerically enriched P,N-ligands, have been compared. The first approach is based on the palladium-catalyzed cross-coupling reaction of halogenated azines with organozinc derivatives of ferrocenes (the Negishi reaction). The second approach exploits a new synthetic methodology, which provides a shorter pathway, through the direct C-H functionalization of aromatics by the C-C coupling of halogen-free (hetero)arenes with lithium ferrocenes bearing stereogenic C and S atoms. The palladium complexes of P,N-ligands have been used as catalysts for the Tsuji-Trost reaction, which proceeds with high enantioselectivity to give allylic substitution products in good yields.

Author keywords:

ASYMMETRIC ALLYLIC ALKYLATION; DIASTEREOSELECTIVE ORTHO-METALATION; DIRECTED ORTHO-LITHIATION; FERROCENYL LIGANDS; NUCLEOPHILIC-SUBSTITUTION; ENANTIOSELECTIVE SYNTHESIS; P,N LIGANDS; 2-SUBSTITUTED FERROCENECARBOXALDEHYDES; 1,3-DIPOLAR CYCLOADDITION; P,N-FERROCENYL LIGANDS

DOI:

10.1021/jo5014299

Web of Science ID:

ISI:000342121100019

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP 19
Publisher	AMER CHEMICAL SOC
Address	1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Language	English
Keywords-Plus	ASYMMETRIC ALLYLIC ALKYLATION; DIASTEREOSELECTIVE ORTHO-METALATION; DIRECTED ORTHO-LITHIATION; FERROCENYL LIGANDS; NUCLEOPHILIC-SUBSTITUTION; ENANTIOSELECTIVE SYNTHESIS; P,N LIGANDS; 2-SUBSTITUTED FERROCENECARBOXALDEHYDES; 1,3-DIPOLAR CYCLOADDITION; P,N-FERROCENYL LIGANDS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	chupakhin@ios.uran.ru
Funding-Acknowledgement	Russian Science Foundation {[}14-13-01177]
Funding-Text	The research was financially supported by the Russian Science Foundation (Project No. 14-13-01177).
Number-of-Cited-References	82
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	39
Journal-ISO	J. Org. Chem.
Doc-Delivery-Number	AP5LQ