Pd-Catalyzed Regiodivergent Hydrocarboxylation of Olefins with Oxalic Acid: A Remarkable Effect of the Counteranion on Regioselectivity

被引：3

作者：

Ren, Wenlong ^{[1
]}

Sheng, Xujian ^{[1
]}

Fan, Chengcheng ^{[1
]}

Shi, Yian ^{[1
]}

机构：

[1] Changzhou Univ, Inst Nat & Synthet Organ Chem, Changzhou 213164, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 43期

基金：

中国国家自然科学基金;

关键词：

FORMIC-ACID; CARBON-MONOXIDE; CARBONYLATION REACTIONS; BRANCHED SELECTIVITY; CARBOXYLIC-ACIDS; PALLADIUM; ALKYNES; ARYL; HYDROXYCARBONYLATION; DERIVATIVES;

D O I：

10.1021/acs.orglett.3c02805

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regioselective Pd-catalyzed hydrocarboxylation of vinyl arenes with oxalic acid is described. A wide variety of either linear or branched carboxylic acids can be readily obtained with high regioselectivities under mild reaction conditions. The reaction process is operationally simple and requires no handling of toxic CO. Besides the ligand, the counteranion of the Pd catalyst system plays an important role in the regioselectivity.

引用

页码：7786 / 7790

页数：5

共 54 条

[1]

Ali B. E., 2002, HDB ORGANOPALLADIUM, P23

[2] Branched Selectivity in the Pd-Catalysed Methoxycarbonylation of 1-Alkenes [J].

Arderne, Charmaine ;

Guzei, llia A. ;

Holzapfel, Cedric W. ;

Bredenkamp, Tyler .

CHEMCATCHEM, 2016, 8 (06) :1084-1093

[3] AN INVESTIGATION OF THE PALLADIUM-CATALYZED, FORMATE-MEDIATED HYDROXYCARBONYLATION OF OPTICALLY-ACTIVE 1-ARYLETHYL ESTERS [J].

BAIRD, JM ;

KERN, JR ;

LEE, GR ;

MORGANS, DJ ;

SPARACINO, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1928-1933

[4] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[5] Palladium-Catalyzed Carbonylation Reactions of Alkenes and Alkynes [J].

Brennfuehrer, Anne ;

Neumann, Helfried ;

Beller, Matthias .

CHEMCATCHEM, 2009, 1 (01) :28-41

[6] Transition-metal-catalyzed transfer carbonylation with HCOOH or HCHO as non-gaseous C1 source [J].

Cao, Jian ;

Zheng, Zhan-Jiang ;

Xu, Zheng ;

Xu, Li-Wen .

COORDINATION CHEMISTRY REVIEWS, 2017, 336 :43-53

[7] Carbonylative synthesis of heterocycles involving diverse CO surrogates [J].

Chen, Zhengkai ;

Wang, Le-Cheng ;

Wu, Xiao-Feng .

CHEMICAL COMMUNICATIONS, 2020, 56 (45) :6016-6030

[8] An effective route to β2-amino acid derivatives via Pd-catalyzed regioselective hydrocarboxylation of 1,2-disubstituted enimides [J].

Dai, Jie ;

Ren, Wenlong ;

Chang, Wenju ;

Zhang, Ping ;

Shi, Yian .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (02) :297-302

[9] A facile approach to β-amino acid derivatives via palladium-catalyzed hydrocarboxylation of enimides with formic acid [J].

Dai, Jie ;

Ren, Wenlong ;

Wang, Haining ;

Shi, Yian .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (31) :8429-8432

[10]

del Río I, 2001, EUR J INORG CHEM, P2719

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