The first example of nickel-catalyzed silyl-Heck reactions: direct activation of silyl triflates without iodide additives

McAtee, Jesse R.; Martin, Sara; Cinderella, Andrew P.; Reid, William B.; Johnson, Keywan A.; Watson, Donald A.

doi:10.1016/j.tet.2014.03.021

Cited by 48 publications

(21 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Using 15 mol % of t BuPCy 2 and 10 mol % Ni(COD) 2 , various styrenes were silylated with trimethylsilyl triflate in good yields (Scheme 14). [18] …”

Section: Silyl-heckmentioning

confidence: 99%

Heck‐Like Reactions Involving Heteroatomic Electrophiles

Vulovic

Watson

2017

Eur J Org Chem

Self Cite

View full text Add to dashboard Cite

Since the discovery of the Heck reaction in the early seventies, this reaction has become a powerful tool in synthetic organic chemistry. By employing heteroatomic instead of traditional carbon electrophiles, the Heck reaction shows an intriguing flexibility. These "hetereoatomic-Heck reactions" reinvigorate the area, offering new routes to highly useful synthetic precursors and structural motifs present in biologically active compounds. This microreview focuses on early developments leading to the heteroatomic-Heck reactions (silyl-Heck, boryl-Heck and intramolecular aza-Heck), current state of the emerging area, as well as that of a few related processes.

show abstract

“…Using 15 mol % of t BuPCy 2 and 10 mol % Ni(COD) 2 , various styrenes were silylated with trimethylsilyl triflate in good yields (Scheme 14). [18] …”

Section: Silyl-heckmentioning

confidence: 99%

Heck‐Like Reactions Involving Heteroatomic Electrophiles

Vulovic

Watson

2017

Eur J Org Chem

Self Cite

View full text Add to dashboard Cite

show abstract

“…6,[13][14][15][16][17][18][19][20] CuI has been used to catalyze the C-S cross-coupling reaction because of its stability to air and good activity with or without the assistance of supporting ligands. [21][22][23][24][25][26] Compared with the above C-S cross-coupling reaction, the application of CuI in the Heck-type reaction is reported less frequently, but there are some successful examples.…”

Section: Scheme 2 the Second-generation Synthesis Routementioning

confidence: 99%

Effective Laboratory-Scale Preparation of Axitinib by Two CuI-Catalyzed Coupling Reactions

Zhai

Guo

Luo

et al. 2015

Org. Process Res. Dev.

View full text Add to dashboard Cite

The discovery and development of an efficient synthesis route to axinitib is reported. The first-generation route researched by Pfizer, implemented two Pd-catalyzed coupling reactions as key steps. In this work, the development of Heck-type and C-S coupling reactions catalyzed by CuI is briefly described, using an economic and practical protocol. Aspects of route, such as selecting ligands, solvent and other conditions are discussed in detail to obtain the optimal conditions. The scale up experiment was carried out to provide more than 300 g active pharmaceutical ingredients (API) of axitinib in Form XLI which was produced with 99.9 % purity in 39 % yield. In short, we provide a new choice of axitinib synthesis route, through two copper-catalyzed coupling reactions with good yield.

show abstract

“…Additionally, the carbon‐bound silicon is readily oxidized, allowing vinylsilanes to serve as masked carbonyl groups 2. We have previously described a silyl‐Heck reaction, which allows for the preparation of unsaturated organosilanes from simple alkenes and electrophilic silanes under palladium catalysis 3,4,5…”

Section: Interplay Of Palladium Precatalyst and Ligand On Yieldmentioning

confidence: 99%

Hydrothermal Synthesis of Two Zinc Coordination Polymers with 1‐(1H‐Tetrazol‐5‐ylmethyl)‐1H‐benzotriazole Ligands

Sun¹,

Jin²,

Shi³

et al. 2013

Zeitschrift anorg allge chemie

View full text Add to dashboard Cite

The direct reaction of ZnBr2 with H‐1‐mbtz [1‐mbtz = 1‐(1H‐tetrazol‐5‐ylmethyl)‐1H‐benzotriazole] gives the two‐dimensional complex [Zn(Br)(1‐mbtz)] (1), whereas the reaction of benzotriazol‐1‐yl‐acetonitrile with NaN3 in the presence of water and a Lewis acid (ZnBr2) affords the 2D coordination polymer [Zn2(OH)(1‐mbtz)3H2O] (2). The central zinc atom in 1 is bonded to one terminal bromine atom and three different nitrogen atoms from two tetrazole ligands and one BTA group (BTA = benzotriazole), and each 1‐mbtz ligand is coordinated to three zinc atoms forming a 2D framework. The coordination polyhedron around the metal atom in 2 is a slightly distorted trigonal bipyramid made up by one zinc atom, four nitrogen atoms as well as one oxygen atom, two of the 1‐mbtz ligands coordinated to three zinc atoms and the third 1‐mbtz ligand acts in a bidentate fashion, which leads to the formation of a complicated 2D network. The syntheses and solid‐state structures of the two coordination polymers are reported.

show abstract

The first example of nickel-catalyzed silyl-Heck reactions: direct activation of silyl triflates without iodide additives

Cited by 48 publications

References 45 publications

Heck‐Like Reactions Involving Heteroatomic Electrophiles

Heck‐Like Reactions Involving Heteroatomic Electrophiles

Effective Laboratory-Scale Preparation of Axitinib by Two CuI-Catalyzed Coupling Reactions

Hydrothermal Synthesis of Two Zinc Coordination Polymers with 1‐(1H‐Tetrazol‐5‐ylmethyl)‐1H‐benzotriazole Ligands

Contact Info

Product

Resources

About