Synthesis of Biaryls through a One‐Pot Tandem Borylation/Suzuki–Miyaura Cross‐Coupling Reaction Catalyzed by a Palladacycle

Wang, Lianhui; Cui, Xiuling; Li, Jingya; Wu, Yusheng; Zhu, Zhiwu; Wu, Yangjie

doi:10.1002/ejoc.201101409

Cited by 42 publications

(18 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Since the discovery of the one‐pot borylation–Suzuki sequence, there has been a steady development of various methods and catalysts which have improved performance and scope . Cui and Wu et al . showed that efficient borylation–Suzuki coupling of heteroaryl bromides could be obtained by using a ferrocenylimine‐palladacycle at 2 mol% of Pd, without the need of additional ligand.…”

Section: Figurementioning

confidence: 99%

One‐Pot Palladium‐Catalyzed Cross‐Coupling Treble of Borylation, the Suzuki Reaction and Amination

et al. 2017

View full text Add to dashboard Cite

Am ethodologyf or as equential palladium-catalyzed cross-coupling procedure consistingo f borylation, the Suzuki reactiona nd amination has been developedf or the assembly of molecules with multi-aryl backbones.T he linchpin of this development is the meta-terarylphosphine ligand, Cy*-Phine,w hich hasb een employed as an air-a nd moisture-stable precatalyst, Pd(Cy*Phine) 2 Cl 2 ,t o improve the efficiency of one-pot borylation-Suzuki reactions.A dditionally,t he reactivity of the Pd-Cy*Phine system could be tuned to furnish ao ne-pot, borylation-Suzuki reaction-amination (BSA) cross-coupling treble.T he methodologys uccessfully integrated complementary conditions for three distinctly different and modular reactions. Average yields of 74-94% could be achieved for each segment that cumulatively afforded 50-84% yield over the entire three-step sequence in as ingle pot.Since the discovery of cross-coupling reactions,t heir applications have grown immensely and are now widelyr egarded as staple organic transformations. As af unction of the areasr apid growth, the number of catalysts developed for this chemistry is vast and has swelled to an extent that catalyst selection has become an increasing challenge.W ith the specialty chemicals andp harmaceutical industries constantly being faced with shrinkingt imelinesa nd product upgrade cycles,s peed to market and process economics are often decisive factors that drive decisions for catalyst selection and process development. Thus,t os idestep the challenges of catalyst selection,c lassical "tried and true" systems, such as Pd(PPh 3 ) 4 ,a re often employed in lieu of more effective, contemporary systems.H owever, as high-throughput screening( HTS) platforms have become more accessible,t he identification of modern catalysts from screeninga rrays can now be achieved much more efficiently than before to improve manufacturing processes,a sw ell as fulfill the demands of compressedtimelines.Previously,o ur group reported the use of a metaterarylphosphine-basedc atalyst, Pd-Cy*Phine,t hat is capable of coupling aryl halides with terminal olefins [1] anda lkynes [2] with notable substrate tolerability and low catalyst loads.Here,wedescribe our developments for the Pd(Cy*Phine) 2 Cl 2 precatalyst used in one-pot multi-step reactions including two-step borylation-Suzuki coupling and three-step borylation-Suzuki-amination (BSA) sequences.Single-pot Pd-catalyzed reactions equencesh ave often been promoted as ac onvenient ande fficient method to synthesize organic compounds. While it may be true that bypassing the isolation of intermediates is attractive, these methods are stilln ot routinely employed. Thea pprehension associated with these one-pot sequences, however, mays oon subside as recent developments have madet hese processes more attractive.Since the discovery of the one-pot borylation-Suzuki sequence, [3] there has been as teady development of various methodsa nd catalysts which have improvedp erformance and scope. [4] Cui and Wu et al. [5] showedt hat efficient borylation-S...

show abstract

Section: Figurementioning

confidence: 99%

One‐Pot Palladium‐Catalyzed Cross‐Coupling Treble of Borylation, the Suzuki Reaction and Amination

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Alternatively, I can also be converted to the corresponding boronic ester IV and subsequently be coupled with 2-chloro-pyridine or its derivatives to introduce the R 1 group at the C5 of the pyrimidine ring. 12 Overall, this route is optimal to explore the structure-activity relationship (SAR) at the R 1 site; it can also be used for SAR exploration at the R 2 and R 3 sites.…”

Section: Chemistrymentioning

confidence: 99%

Pseudo-Cyclization through Intramolecular Hydrogen Bond Enables Discovery of Pyridine Substituted Pyrimidines as New Mer Kinase Inhibitors

Zhang¹,

Zou²,

Stashko³

et al. 2013

J. Med. Chem.

View full text Add to dashboard Cite

Abnormal activation or overexpression of Mer receptor tyrosine kinase has been implicated in survival signaling and chemoresistance in many human cancers. Consequently, Mer is a promising novel cancer therapeutic target. A structure-based drug design approach using a pseudo-ring replacement strategy was developed and validated to discover a new family of pyridinepyrimidine analogs as potent Mer inhibitors. Through SAR studies, 10 (UNC2250) was identified as the lead compound for further investigation based on high selectivity against other kinases and good pharmacokinetic properties. When applied to live cells, 10 inhibited steady-state phosphorylation of endogenous Mer with an IC50 of 9.8 nM and blocked ligand-stimulated activation of a chimeric EGFR-Mer protein. Treatment with 10 also resulted in decreased colony-forming potential in rhabdoid and NSCLC tumor cells, thereby demonstrating functional anti-tumor activity. The results provide a rationale for further investigation of this compound for therapeutic application in patients with cancer.

show abstract

“…Some useful recent examples include the work of Wang et al [157], which involved a one-pot borylation/Suzuki-Miyaura reaction. Some useful recent examples include the work of Wang et al [157], which involved a one-pot borylation/Suzuki-Miyaura reaction.…”

Section: Recent New Developments 67mentioning

confidence: 99%

Cross‐Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

2014

Catalytic Arylation Methods

View full text Add to dashboard Cite

Synthesis of Biaryls through a One‐Pot Tandem Borylation/Suzuki–Miyaura Cross‐Coupling Reaction Catalyzed by a Palladacycle

Cited by 42 publications

References 58 publications

One‐Pot Palladium‐Catalyzed Cross‐Coupling Treble of Borylation, the Suzuki Reaction and Amination

One‐Pot Palladium‐Catalyzed Cross‐Coupling Treble of Borylation, the Suzuki Reaction and Amination

Pseudo-Cyclization through Intramolecular Hydrogen Bond Enables Discovery of Pyridine Substituted Pyrimidines as New Mer Kinase Inhibitors

Cross‐Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

Contact Info

Product

Resources

About