Transition-Metal-Catalyzed Facile Access to 3,11-Dialkylfulminenes for Transistor Applications

Murai, Masahito; Maekawa, Hiroyuki; Hamao, Shino; Kubozono, Yoshihiro; Roy, David; Takai, Kazuhiko

doi:10.1021/ol503723j

Cited by 22 publications

(25 citation statements)

References 33 publications

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“…[7d] This synthesis consisted of ruthenium-catalyzed direct CÀHa rylation, [12] followed by sequential Wittig olefination and bismuth-catalyzed cyclization of the resulting vinyl ethers (Scheme 3). [13] Based on this success, we initially attempted the synthesis of 3,10-disilyl [5]phenacene( 2)a nd 3,12-disilyl [7]phenacene (3)t hrough as imilar three-step synthesis strategy. However,i nt he first reactiont hat we attempted, the ruthenium-catalyzed direct CÀHa rylations of aldimines that were derived from 3-silylbenzaldehyde with 1,4-dibromobenzene (Scheme 4a)o r1 ,8-diformylphenanthrenew ith bromo-4-silyl-benzene (Scheme 4b)d id not proceed efficiently.…”

Section: Resultsmentioning

confidence: 99%

“…In view of these results, we decided to change the synthetic route, as showni nS cheme 5. This new designh as the advantage of allowing the synthesis of both [5]-and [7]phenacenes from ac ommon synthetic intermediate, 1-formyl-7phenanthrene (9), without the requirement for at wo-fold direct CÀHa rylation reaction.…”

Section: Resultsmentioning

confidence: 99%

“…After heatinga tr eflux in CH 2 Cl 2 with triphenylphosphine, the resultingp hosphonium salts were treated witha ldehyde 9 and K 2 CO 3 to furnishd iphenanthryl ethylene 12 as am ixture of E and Z stereoisomers. Photocyclization under irradiation by aU Vlamp in the presence of Scheme2.Structures of the target [5]-and [7]phenacenes with silyl groups at the axis positions.…”

Section: Resultsmentioning

confidence: 99%

“…Asian J. 2015, 10,2518 -2524 www.chemasianj.org iodine yielded3 ,12-di(trimethylsilyl) [7]phenacene (3)i n4 6% yield. This is ar are example of the synthesis of functionalized [n]phenacenes (n > 6).…”

Section: Resultsmentioning

confidence: 99%

“…However,a lthough numerouss tudies have investigated the transition-metal-catalyzed synthesis of fused polyaromatic hydrocarbons, [6] their application to the short and efficient synthesis of functionalized[ n]phenacenes has so far been limited. [7] To further develop the unique properties of [n]phenacenes, we investigated short transition-metal-catalyzed syntheses of [n]phenacenes that contained appropriate functional groups at the axis positions. Thisd esign was inspired by ar ecent mobility study of 3,10-di(tetradecyl) [5]phenacene (1a)b yK ubozono and co-workers( Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Short Synthesis of [5]‐ and [7]Phenacenes with Silyl Groups at the Axis Positions

Roy

Maekawa

Murai

et al. 2015

Chemistry An Asian Journal

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[5]Phenacene with trimethylsilyl groups at the axis positions was synthesized by the ruthenium-catalyzed direct C-H arylation of a 1-formyl-7-phenanthrene-derived aldimine, followed by sequential Wittig olefination and bismuth-catalyzed cyclization of the resulting vinyl ethers. By using the same synthetic building blocks and sequential Wittig olefination and photocyclization, the number of fused benzene rings was readily increased to seven to afford 3,12-disilyl[7]phenacene. The introduction of silyl groups endowed the [n]phenacene frameworks with good solubility, as well as enabling further functionalization. The electronic structure of these new [n]phenacenes was determined by photophysical measurements and by density functional theory calculations, which clearly implied effective conjugation throughout the entire π framework.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Short Synthesis of [5]‐ and [7]Phenacenes with Silyl Groups at the Axis Positions

Roy

Maekawa

Murai

et al. 2015

Chemistry An Asian Journal

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Palladium‐Catalyzed Direct Arylation of Azulene Based on Regioselective C−H Bond Activation

et al. 2016

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An efficient synthesis of arylazulenes involving minimal steps was developed. The combination of Pd(OAc) 2 / XPhos as ac atalysta nd pivalica cid as an additive was key for the direct arylation of CÀHb onds, and the reactionp roceeded preferentially at the 1-and 3-positions of azulene, without heteroatom-containing directing groups. Compared with the traditional cross-coupling protocol, the arylation method described here requires fewer steps and uses commerciallya vailables ynthetic blocks. The degree of conjugation and the optical properties of the resulting azulenec onjugates can be adjusted by simple protonation, whicha llows the current method to be an efficient strategy for exploiting novel azulene-based functional materials.[a] Dr.

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Synthesis, Photophysical and Electrochemical Study of 1,3,6,8‐Tetraarylsubstituted X‐Shaped Phenanthrene Derivatives

2022

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X‐shaped phenanthrene derivatives containing aryl substituents at the 1,3,6,8‐positions were synthesized through Suzuki coupling reactions of two types of phenanthrenes possessing bromine and chlorine substituents. X‐shaped phenanthrenes, with four t‐butylphenyl, 9,9‐dimethyl‐9H‐fluoren‐2‐yl or 4‐diphenylaminophenyl (DPAP) groups, are highly emissive in the blue region and their fluorescence efficiencies increase as the extent of aryl π‐conjugation increases. To assess the effects of donor (D) and acceptor (A) groups at the 1,8‐ and 3,6‐positions on intramolecular charge‐transfer emission, two D−A compounds with two DPAP D‐groups and two 4‐pyridyl (Py) A‐groups were synthesized. Results of electrochemical studies reveal that the phenanthrene with four DPAP groups does not undergo oxidative polymerization in dichloromethane, but the two D−A analogs possessing both DPAP and Py groups do undergo oxidative polymerization, producing films which have electrochromic properties.

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Transition-Metal-Catalyzed Facile Access to 3,11-Dialkylfulminenes for Transistor Applications

Cited by 22 publications

References 33 publications

Short Synthesis of [5]‐ and [7]Phenacenes with Silyl Groups at the Axis Positions

Short Synthesis of [5]‐ and [7]Phenacenes with Silyl Groups at the Axis Positions

Palladium‐Catalyzed Direct Arylation of Azulene Based on Regioselective C−H Bond Activation

Synthesis, Photophysical and Electrochemical Study of 1,3,6,8‐Tetraarylsubstituted X‐Shaped Phenanthrene Derivatives

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