Rapid Construction of Fused Heteropolycyclic Aromatics via Palladium-Catalyzed Domino Arylations of Imidazopyridine Derivatives

Xue, Chenwei; Han, Jianwei; Zhao, Min; Wang, Limin

doi:10.1021/acs.orglett.9b00761

Cited by 42 publications

(24 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several advantages such as reduction of the synthetic steps and no production of stoichiometric amount of toxic by-products are provided by using domino arylations of imidazopyridine derivatives. In this context, a palladium-catalyzed direct arylation of 2-phenylimidazo[1-α]pyridine using diphenyliodonium triflate as a coupling partner was described by Wang et al [89]. The screening of the reaction conditions revealed that using K 2 CO 3 as the base and Pd(OAc) 2 (10 mol%) as a catalyst in DMF at 100 • C for 24 h led to the selective C3-phenylation in 91% (Scheme 18).…”

Section: Introductionmentioning

confidence: 99%

Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

2020

View full text Add to dashboard Cite

Owing to the pioneering works performed on the metal-catalyzed sp2 C–H arylation of indole and pyrrole by Sanford and Gaunt, N– and C-arylation involving diaryliodonium salts offers an attractive complementary strategy for the late-stage diversification of heteroarenes. The main feature of this expanding methodology is the selective incorporation of structural diversity into complex molecules which usually have several C–H bonds and/or N–H bonds with high tolerance to functional groups and under mild conditions. This review summarizes the main recent achievements reported in transition-metal-catalyzed N– and/or C–H arylation of heteroarenes using acyclic diaryliodonium salts as coupling partners.

show abstract

Section: Introductionmentioning

confidence: 99%

Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

2020

View full text Add to dashboard Cite

show abstract

“…All the starting materials and reagents for the synthesis were obtained from commercial suppliers and directly used without further purification. First, compounds IP‐Br, 1 , and 2 were prepared as reported . A one‐step Suzuki palladium‐catalyzed cross‐coupling reaction was used to synthesize the target products IP‐PPI and IP‐DPPI.…”

Section: Resultsmentioning

confidence: 99%

“…First, compoundsI P-Br, 1,a nd 2 were prepared as reported. [19,30] Ao ne-step Suzuki palladium-catalyzedc ross-coupling reactionw as used to synthesize the target products IP-PPI and IP-DPPI. The crude product was purified by silica column chromatography and characterizedw ith 1 HNMR spectroscopy, mass spectrometry,and elemental analysis.…”

Section: Synthesismentioning

confidence: 99%

Imidazo[1,2‐a]pyridine as an Electron Acceptor to Construct High‐Performance Deep‐Blue Organic Light‐Emitting Diodes with Negligible Efficiency Roll‐Off

Zheng

Zhao

Chen

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

Twon ovel bipolar deep-bluef luorescent emitters, IP-PPI and IP-DPPI, featuring different lengths of the phenyl bridge,w ere designed and synthesized, in which imidazo[1,2-a]pyridine (IP) andp henanthroimidazole (PI) were proposed as an electron acceptor and an electron donor,r espectively.Both of them exhibit outstanding thermal stability and high emission quantumy ields. All the devices based on these two materials showedn egligible efficiency roll-off with increasing current density.I mpressively,n on-doped organic light-emitting diodes (OLEDs) based on IP-PPI and IP-DPPI exhibited externalq uantum efficiencies(EQEs) of 4.85 %a nd 4.74 %w ith CIE coordinates of (0.153, 0.097) and (0.154, 0.114) at 10000cdm À2 ,r espectively.I na ddition, the 40 wt % IP-PPI doped device maintained ah igh EQE of 5.23 %w ith CIE coordinates of (0.154, 0.077) at 10000 cd m À2 .T he doped deviceb ased on 20 wt %I P-DPPIe xhibited ah igher deepblue electroluminescence (EL) performance with am aximum EQE of up to 6.13 %a tC IE of (0.153,0 .078) and maintained an EQE of 5.07 %a t1 0000 cd m À2 .T ot he best of our knowledge,t hese performances are among the state-of-thea rt devices with CIE y 0.08 at ah igh brightness of 10000cdm À2. Furthermore, by doping ar ed phosphorescent dye Ir(MDQ) 2 (MDQ = 2-methyldibenzo[f,h]quinoxaline) into the IP-PPI and IP-DPPI hosts, high-performance red phosphorescentO LEDs with EQEs of 20.8 %a nd 19.1 %w ere achieved, respectively. This work may provide an ew approach for designinghighly efficient deep-blue emitters with negligible roll-off for OLED applications.

show abstract

“…Diarylation and subsequent intramolecular cyclization of 2‐phenylimidazo[1, 2‐ a ]pyridine derivatives with diaryliodonium salts was reported by Xue and his co‐workers in 2019 (Scheme 24). [50] One important observation of this methodology is that except acetic acid no other solvents result in the desired product. The reaction proceeds smoothly for electronically varied 2‐phenylimidazo[1, 2‐ a ]pyridine scaffolds.…”

Section: Functionalization Reactions Of Imidazo[1 2‐a]pyridinementioning

confidence: 99%

Recent Developments in Transition‐Metal‐Catalyzed Regioselective Functionalization of Imidazo[1, 2‐a]pyridine

Konwar

Bora

2021

ChemistrySelect

View full text Add to dashboard Cite

Imidazo[1,2‐a]pyridine is an important nitrogen‐containing heterocycle from biological as well as pharmaceutical point of view. In recent years, regioselective functionalization of C−H bond of imidazo[1,2‐a]pyridine is extensively carried out using various transition metal‐based catalysts. Alkenylation, arylation, dual dehydrogenative annulations, formylation, thiolation, aminomethylation, dicarbonylation, phosphonylation along with other significant reactions are the progress in the field of functionalization of imidazopyridine. Most of these functionalizations are done at the C‐3 position of imidazo[1,2‐a]pyridine scaffold and in addition to that development towards C‐5 regioselectivity is also available. In this review, our aim is to present the recent advances for the functionalization of imidazo[1,2‐a]pyridine employing transition metal catalysts under significant reaction conditions.

show abstract

Rapid Construction of Fused Heteropolycyclic Aromatics via Palladium-Catalyzed Domino Arylations of Imidazopyridine Derivatives

Cited by 42 publications

References 51 publications

Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

Imidazo[1,2‐a]pyridine as an Electron Acceptor to Construct High‐Performance Deep‐Blue Organic Light‐Emitting Diodes with Negligible Efficiency Roll‐Off

Recent Developments in Transition‐Metal‐Catalyzed Regioselective Functionalization of Imidazo[1, 2‐a]pyridine

Contact Info

Product

Resources

About