Recent advances in direct dehydrogenative biphenyl couplings

Lv, Fei; Yao, Zhu‐Jun

doi:10.1007/s11426-016-0435-5

Cited by 17 publications

(7 citation statements)

References 48 publications

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“…Arene‐arene coupling in the Scholl process proceeds through a cationic intermediate which is either arenium or radical in nature [14] . The remaining alternative of radical anion coupling is rare [15] . In contrast to anionic pyridine‐pyridine coupling, [16] there are only scarce examples for benzene‐benzene coupling via an anionic intermediate.…”

Section: Methodsmentioning

confidence: 99%

“…[14] The remaining alternative of radical anion coupling is rare. [15] In contrast to anionic pyridinepyridine coupling, [16] there are only scarce examples for benzene-benzene coupling via an anionic intermediate. Benzene does not react with alkali metals but cocondensation of K, Rb or Cs with benzene resulted in C 6 H 6 *À salts and radical coupling to (biphenyl) 2À and H 2 .…”

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confidence: 99%

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Alkaline‐Earth Metal Mediated Benzene‐to‐Biphenyl Coupling

et al. 2022

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Complex [( DIPeP BDI)Ca] 2 (C 6 H 6 ), with a C 6 H 6 2À dianion bridging two Ca 2 + ions, reacts with benzene to yield [( DIPeP BDI)Ca] 2 (biphenyl) with a bridging biphenyl 2À dianion ( DIPeP BDI = HC[C(Me)N-DIPeP] 2 ; DIPeP = 2,6-CH(Et) 2 -phenyl). The biphenyl complex was also prepared by reacting [( DIPeP BDI)Ca] 2 (C 6 H 6 ) with biphenyl or by reduction of [( DIPeP BDI)CaI] 2 with KC 8 in presence of biphenyl. Benzene-benzene coupling was also observed when the deep purple product of ballmilling [( DIPP BDI)CaI(THF)] 2 with K/KI was extracted with benzene (DIPP = 2,6-CH(Me) 2 -phenyl) giving crystalline [( DIPP BDI)Ca(THF)] 2 (biphenyl) (52 % yield). Reduction of [( DIPeP BDI)SrI] 2 with KC 8 gave highly labile [( DIPeP BDI)Sr] 2 (C 6 H 6 ) as a black powder (61 % yield) which reacts rapidly and selectively with benzene to [( DIPeP BDI)Sr] 2 (biphenyl). DFT calculations show that the most likely route for biphenyl formation is a pathway in which the C 6 H 6 2À dianion attacks neutral benzene. This is facilitated by metal-benzene coordination.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Alkaline‐Earth Metal Mediated Benzene‐to‐Biphenyl Coupling

et al. 2022

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“…It is worth Recently, C-H functionalizations, in particular metal-catalyzed, have gained a remarkable attention in terms of issued reviews. 6,[10][11][12][13][14][15][16][17][18][19] This includes a selection of catalytic reagents, the types of transformations. As for oxidants impact, in particular, in functionalization of С(sp 2 )-H in heteroarenes, no attempt to capture data in a systematic way has been made until this review despite a fundamental role of an oxidizing agent.…”

Section: Figure 2 Metal-free Oxidative C-h Functionalization (Sn H Re...mentioning

confidence: 99%

Oxidizing agents in metal-catalyzed and metal-free C-H functionalization of heteroarenes

Utepova¹,

Чупахин²,

Trestsova³

et al. 2021

Arkivoc

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Oxidative C-H functionalization represents a crucial method to make new C-C, C-X (X = heteroatom) bonds. An optimal selection of the oxidizing agent goes hand in hand with the insight into the reaction mechanism. This review covers recent advances in methods of direct oxidative C-H functionalization of azines and their derivatives with heteroaromatic nucleophiles. Also we review the data on application of inorganic and organic oxidants for implementation of these reactions. C-H functionalizations under electrochemical and photocatalytic oxidation conditions are included as well.

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“…The construction of organic conjugated molecules depends on the efficient formation of the carbon-carbon bond between two sp 2 carbons [23][24][25][26][27]. For this purpose, a variety of carbon-carbon cross-coupling reactions, such as Suzuki, Stille, Heck, and Kumada reactions, have thus been widely explored for the couplings of aryl halides with the toxic intermediates (organometallic/boride heteroaromatics) [28][29][30][31][32][33]. In contrast, direct C-H arylation overcomes the use of toxic intermediates and simplifies the reaction process, which has emerged most recently as a simple, atom-efficient, and ecofriendly methodology for constructing conjugated molecules, especially for those containing electron-deficient moieties [34][35][36][37][38][39].…”

Section: Introductionmentioning

confidence: 99%

Highly Regioselective Direct C-H Arylation: Facile Construction of Symmetrical Dithienophthalimide-Based π -Conjugated Molecules for Optoelectronics

Xue

Song

et al. 2020

Research

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Controllable direct C-H arylation with high regioselectivity is highly desirable yet remains a formidable challenge. Herein, a facile regioselective direct C-H arylation is developed for efficient construction of a variety of symmetrical dithienophthalimide-based π-conjugated molecules. The resulting methodology is applicable to a wide range of substrates, from electron-rich units to electron-deficient units with large steric end groups. Aryl halides have been confirmed to be able to couple with dithienophthalimide (DTI) via direct C-H arylation, showing high regioselectivity. Varying the functional end groups onto the DTI core has been demonstrated to fine tune the emission colors to cover most of the visible spectra. The results suggest a facile strategy towards highly selective direct C-H arylation, opening the prospects towards efficient construction of π-conjugated molecules for various potential optoelectronic applications.

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Recent advances in direct dehydrogenative biphenyl couplings

Cited by 17 publications

References 48 publications

Alkaline‐Earth Metal Mediated Benzene‐to‐Biphenyl Coupling

Alkaline‐Earth Metal Mediated Benzene‐to‐Biphenyl Coupling

Oxidizing agents in metal-catalyzed and metal-free C-H functionalization of heteroarenes

Highly Regioselective Direct C-H Arylation: Facile Construction of Symmetrical Dithienophthalimide-Based π -Conjugated Molecules for Optoelectronics

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