2- Modified Catellani’s Reaction: Marc and Christophe 3- Rhodium Chemistry: Raphaël, Romain and Sébastien 4- Cyclopropanes Chemistry: Thomas and Corinne 5- Oxa- and Azabicycles Ring Opening: Marie-Alice, Mathieu and Aurélie

ABSTRACT: The Catellani reaction provides a facile and eﬃcient method for the synthesis of multifunctionalized arenes. However, the use of Pd(0) catalysts restricts the scope of accessible products. We have developed a Pd(II)-catalyzed, Catellani-type reaction utilizing arylboronic acids as the substrates for the ﬁrst time.

2015-10-22 · The Catellani reaction — a palladium-catalysed C–H functionalization reaction mediated by norbornene — was first reported in 1997. The capacity to functionalize both the ortho and ipso III. Product isolation of Heck-Catellani Reaction of aromatic bromides. Typical procedure for isolation: In an argon-filled glove box, a dry 10-mL Schlenk tube containing a magnetic stirbar was charged with Pd(dba) 2 (11.5 mg, 0.02 mmol), PtBu 3 ·HBF 4 (11.5 mg, 0.03 mmol) and dry DMF (1.0 mL). After stirring at RT for 10 These intermediates have been a long-standing focus of the Catellani-reaction development, but persistent challenges have given rise to the well-known “ ortho effect.” We now show that the ortho effect can be a positive element of reaction design, and that previously problematic iodides can now be used in complexity-generating transformations. These intermediates have been a long-standing focus of the Catellani-reaction development, but persistent challenges have given rise to the well-known “ ortho effect.” We now show that the ortho effect can be a positive element of reaction design, and that previously problematic iodides can now be used in complexity-generating transformations. We describe herein a new method that allows selective production of Catellani–Heck isomers from various aryl halides, including ones without ortho -groups. Under previous conditions, unhindered aryl halides were plagued with the formation of simple Heck isomers and multiple arylation and norbornene insertion.

This borono-Catellani reaction was promoted by cooperative c … Abstract A palladium-catalyzed and norbornene-mediated Catellani reaction was developed through ortho-acylation and ipso-alkynylation for the aryl iodides. Acyl chlorides were used as acylation reagents and phenylpropiolic acids were used as termination reagents respectively in this transformation. As a result, the reactivity of these three different compounds matched well and this unreported 2017-11-30 Achieving high selectivity through multiple C–H functionalization is a challenging task. In this issue of Chem, Lumb, Luan, and co-workers disclose a clever strategy taking advantage of steric remote effects for the synthesis of poly-substituted arenes through a 4-component Catellani reaction with remarkable regio- and chemoselectivity by using readily available reagents. Request PDF | Modular and regioselective synthesis of all-carbon tetrasubstituted olefins enabled by an alkenyl Catellani reaction | All-carbon tetrasubstituted olefins have been found in numerous 2015-11-01 2019-11-18 2009-10-14 2013-12-17 Alkyl Tosylates as Alkylating Reagents in the Catellani Reaction Qianwen Gao a Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China Email: hgcheng@whu.edu.cn Email: qhzhou@whu.edu.cn We report a cooperative catalytic system comprising a PdII complex, XPhos, and the potassium salt of 5‐norbornene‐2‐carboxylic acid that enables the use of epoxides as alkylating reagents in the Catellani reaction, thereby expanding the existing paradigm of this powerful transformation.

This borono-Catellani reaction was promoted by cooperative catalysis between Pd(OAc) 2 and the inexpensive 5-norbornene-2-carbonitrile. Practicality is the striking feature of the reaction: it is run open to air at ambient temperature and no phosphine ligand is needed. Through application of the Catellani reaction, a great number of diverse scaffolds have been synthesized in one pot from simple starting materials.

This report describes the first application of a cyclobutanol ring-opening procedure in the Catellani termination reaction, which includes two β-carbon elimination processes. This tandem reaction features mild conditions, high yields, good functional group tolerance, and a broad substrate scope.

33 Conclusions Catellani reaction is a useful and mechanistically interesting method for the polyfunctionalization of aromatic molecules. The Catellani reaction — a palladium-catalysed C–H functionalization reaction mediated by norbornene — was first reported in 1997. The capacity to functionalize both the ortho and ipso positions of ABSTRACT: The Catellani reaction provides a facile and eﬃcient method for the synthesis of multifunctionalized arenes. However, the use of Pd(0) catalysts restricts the scope of accessible products.

Catellani 反应 (Catellani Reaction) Catellani反应是多组分 (3-component reaction)偶联反应中的一种。. 该反应中，在降冰片烯 (Norbornene)与Pd共同催化作用下，首先发生溝呂木-Heck反应，然后活化邻位苯环上的H，最后与卤代烷烃进行C-C偶联得到最终产物。. (详见反应机理) Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 119.

of K 2 CO 3 in DMF at 105 °C for 1 h. The Catellani reaction was discovered by Marta Catellani (Università degli Studi di Parma, Italy) and co-workers in 1997. [1] [2] The reaction uses aryl iodides to perform bi- or tri-functionalization, including C-H functionalization of the unsubstituted ortho position(s), followed a terminating cross-coupling reaction at the ipso position. borono-Catellani reaction to achieve the ortho-C−H alkylation of arylboronicacidsandesters.6,7 Inspiredby thischemistry,we envisaged that the aforementioned poor chemoselectivity issue in Pd0/NBE catalyzed unsymmetrical arylation might be solved through the distinct PdII/NBE catalyzed “borono-Catellani (2014) Bibliographical Background: The Ortho Effect in The Catellani Reaction. In: Development of New Radical Cascades and Multi-Component Reactions. Springer Theses (Recognizing Outstanding Ph.D. Research).

Acyl chlorides were used as acylation reagents and phenylpropiolic acids were used as termination reagents respectively in this transformation. As a result, the reactivity of these three different compounds matched well and this unreported 2017-11-30 Achieving high selectivity through multiple C–H functionalization is a challenging task. In this issue of Chem, Lumb, Luan, and co-workers disclose a clever strategy taking advantage of steric remote effects for the synthesis of poly-substituted arenes through a 4-component Catellani reaction with remarkable regio- and chemoselectivity by using readily available reagents. Request PDF | Modular and regioselective synthesis of all-carbon tetrasubstituted olefins enabled by an alkenyl Catellani reaction | All-carbon tetrasubstituted olefins have been found in numerous 2015-11-01 2019-11-18 2009-10-14 2013-12-17 Alkyl Tosylates as Alkylating Reagents in the Catellani Reaction Qianwen Gao a Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China Email: hgcheng@whu.edu.cn Email: qhzhou@whu.edu.cn We report a cooperative catalytic system comprising a PdII complex, XPhos, and the potassium salt of 5‐norbornene‐2‐carboxylic acid that enables the use of epoxides as alkylating reagents in the Catellani reaction, thereby expanding the existing paradigm of this powerful transformation. The potassium salt of inexpensive 5‐norbornene‐2‐carboxylic acid acts as both mediator and base Reaction mechanism.
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The capacity to functionalize both the ortho and ipso III. Product isolation of Heck-Catellani Reaction of aromatic bromides.

Catellani.png 1,334 × 1,344; 54 KB. 2017-11-30 · Catellani and co-workers reported that the reaction of iodobenzenes with o-bromobenzylic alcohols bearing no benzylic hydrogen proceeded in the presence of a palladium catalyst and NBE to produce dibenzopyrans.12 According to their procedure, 2a and 3a were treated with 5 mol% Pd(OAc) 2, 1 equiv. of NBE, and 2.5 equiv. of K 2 CO 3 in DMF at 105 °C for 1 h.
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2018-08-02 · Catellani reaction This cross-coupling cascade reaction . K2CO the reaction of 4-iodo-2-quinolones with tertiary o-bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields.

AICE. 2009,1849 Catellani M. Tetrahedron Lett, 2004(45),6903-6907. 33 Conclusions Catellani reaction is a useful and mechanistically interesting method for the polyfunctionalization of aromatic molecules. The Catellani reaction — a palladium-catalysed C–H functionalization reaction mediated by norbornene — was first reported in 1997.