Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones

被引：12

作者：

Kattela, Shivashankar ^{[1
,2
]}

Correia, Carlos Roque D. ^{[3
]}

Ros, Abel ^{[1
,2
]}

Hornillos, Valentin ^{[1
,2
,4
]}

Iglesias-Sigu, Javier ^{[2
,4
]}

Fernandez, Rosario ^{[2
,4
]}

Lassaletta, Jose M. ^{[1
,2
]}

机构：

[1] Inst Invest Quim CSIC US, Seville 41092, Spain

[2] Ctr Innovac Quim Avanzada ORFEO CINQA, Seville 41092, Spain

[3] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP, Brazil

[4] Univ Seville, Dept Quim Organ, Seville 41012, Spain

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 21期

基金：

巴西圣保罗研究基金会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; DIAZOCARBONYL COMPOUNDS; MIGRATORY INSERTION; CONSTRUCTION; RESOLUTION; DESYMMETRIZATION; REAGENTS; LIGANDS; ALKYNES;

D O I：

10.1021/acs.orglett.2c01355

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A dynamic kinetic asymmetric Pd-catalyzed cross-coupling reaction of heterobiaryl bromides with ketone N-tosylhydrazones for the synthesis of heterobiaryl styrenes is described. The combination of Pd(dba)(2) as a precatalyst with a TADDOL-derived phosphoramidite ligand provides the corresponding coupling products in good yields and high enantioselectivities under mild conditions. Racemization-free N-oxidation and N-alkylation of the products allowed us to obtain appealing functionalized axially chiral heterobiaryl derivatives.

引用

页码：3812 / 3816

页数：5

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