Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates

We present a mechanistic investigation of Pd-catalyzed allylic substitution of cyclic gem-difluorinated carbonates 1 and 4, previously employed in the synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides in 17 steps. The substitution feature...

Full description

Bibliographic Details
Main Authors:	Jun Xu, Xiao-Long Qiu, Feng-Ling Qing
Format:	Article
Language:	English
Published:	Beilstein-Institut 2008-05-01
Series:	Beilstein Journal of Organic Chemistry
Online Access:	https://doi.org/10.3762/bjoc.4.18

id	doaj-8af97623a56147f4aa9d2990d6c0ea20
record_format	Article
spelling	doaj-8af97623a56147f4aa9d2990d6c0ea202021-02-02T01:38:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972008-05-01411810.3762/bjoc.4.181860-5397-4-18Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonatesJun Xu0Xiao-Long Qiu1Feng-Ling Qing2Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, ChinaKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, ChinaKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, ChinaWe present a mechanistic investigation of Pd-catalyzed allylic substitution of cyclic gem-difluorinated carbonates 1 and 4, previously employed in the synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides in 17 steps. The substitution features a reversal of regioselectivity caused by fluorine.https://doi.org/10.3762/bjoc.4.18
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Jun Xu Xiao-Long Qiu Feng-Ling Qing
spellingShingle	Jun Xu Xiao-Long Qiu Feng-Ling Qing Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates Beilstein Journal of Organic Chemistry
author_facet	Jun Xu Xiao-Long Qiu Feng-Ling Qing
author_sort	Jun Xu
title	Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title_short	Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title_full	Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title_fullStr	Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title_full_unstemmed	Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
title_sort	understanding the mechanism of pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2008-05-01
description	We present a mechanistic investigation of Pd-catalyzed allylic substitution of cyclic gem-difluorinated carbonates 1 and 4, previously employed in the synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides in 17 steps. The substitution features a reversal of regioselectivity caused by fluorine.
url	https://doi.org/10.3762/bjoc.4.18
work_keys_str_mv	AT junxu understandingthemechanismofpdcatalyzedallylicsubstitutionofthecyclicdifluorinatedcarbonates AT xiaolongqiu understandingthemechanismofpdcatalyzedallylicsubstitutionofthecyclicdifluorinatedcarbonates AT fenglingqing understandingthemechanismofpdcatalyzedallylicsubstitutionofthecyclicdifluorinatedcarbonates
_version_	1724311394931703808

Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates

Similar Items