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Nickel-Catalyzed Regiodivergent Reductive Hydroarylation of Styrenes
We report a ligand-controlled nickel-catalyzed reductive hydroarylation of styrenes with predictable and controllable regioselectivity. With a diamine ligand, the reaction produces selective linear hydroarylation products. Alternatively, with a chiral PyrOx ligand, branch-selective enantioenriched 1,1-diarylalkane products are obtained. Preliminary mechanistic results are consistent with a reductive Heck process.
Xue, Yuhang,Chen, Jian,Song, Peihong,He, Yuli,Zhu, Shaolin
supporting information
p. 1647 - 1651
(2021/07/02)

"bulky-Yet-Flexible" α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air
To pursue a highly regioselective and efficient reductive Heck reaction, a series of moisture-and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the"bulky-yet-flexible"palladium complexes allowed highly anti-Markovnikov-selective hydroarylation of alkenes with (hetero)aryl bromides under aerobic conditions. Further synthetic application of the present protocol could provide rapid and straightforward access to functional and biologically active molecules.
Yang, Xu-Wen,Li, Dong-Hui,Song, A-Xiang,Liu, Feng-Shou
p. 11750 - 11765
(2020/10/23)

CARBAMATE DERIVATIVES AND USES THEREOF
The present disclosure relates to compounds of Formula (I): and to their prodrugs, pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for inhibiting the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as inflammatory, autoinflammatory and autoimmune diseases and cancers.
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Paragraph 01446

(2020/08/13)

Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate
The generation of tertiary, secondary, and primary alkyl radicals has been achieved by the direct visible-light excitation of a boracene-based alkylborate. This system is based on the photophysical properties of the organoboron molecule. The protocol is applicable to decyanoalkylation, Giese addition, and nickel-catalyzed carbon-carbon bond formations such as alkyl-aryl cross-coupling or vicinal alkylarylation of alkenes, enabling the introduction of various C(sp3) fragments to organic molecules.
Hashizume, Daisuke,Hosoya, Takamitsu,Nakamura, Kei,Ohmiya, Hirohisa,Sato, Yukiya,Sumida, Yuto
supporting information
p. 9938 - 9943
(2020/06/27)

Application of novel coupling reaction to preparing carbon-carbon bond structured compounds
The invention relates to application of a novel coupling reaction to preparing carbon-carbon bond structured compounds and mainly provides a reaction between alkyl indium compounds and halides. The reaction between the alkyl indium compounds and the halides can produce corresponding carbon-carbon structured products. The novel coupling reaction is high in process yield, broad in functional group tolerance and good in compatibility.
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Paragraph 0099-0103

(2019/06/30)

Copper(II)-catalyzed preparation of alkylindium compounds and applications in cross-coupling reactions both in aqueous media
An efficient water-based method for the synthesis of alkylindium compound in the presence of a catalytic amount of cheap and readily available CuSO4·5H2O (10 mol%) was developed. The thus-generated alkylindium compounds effectively underwent palladium-catalyzed cross-coupling reactions with a myriad of aryl halides in aqueous media, leading to the cross-coupled products in modest to high yields. The mildness of the formed alkyl organometallics allowed the tolerance to various important functional groups incorporated in both substrates of alkyl iodides and aryl halides.
Wang, Peng,Chen, Bing-Zhi,Guo, Yi-Cong,Rao, Weidong,Shen, Zhi-Liang
supporting information

(2019/11/11)

Cobalt(II)-catalyzed preparation of alkylindium reagents and applications in cross-coupling with aryl halides
The direct insertion of indium powder into alkyl iodides was found to be efficiently catalyzed by a catalytic amount of cobalt(II) bromide (10 mol%). Upon subjection of the thus-formed alkylindium compounds to palladium-catalyzed cross-coupling reactions with a wide range of aryl halides, a series of cross-coupled products could be obtained in moderate to good yields with the tolerance to many important functional groups.
Wang, Peng,Song, Xuan-Di,Chen, Bing-Zhi,Rao, Weidong,Shen, Zhi-Liang
(2019/10/16)

Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions
An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate for indium insertion with equal ease.
Zhi, Man-Ling,Chen, Bing-Zhi,Deng, Wei,Chu, Xue-Qiang,Loh, Teck-Peng,Shen, Zhi-Liang
p. 3017 - 3023
(2019/02/26)

Cesium carbonate-catalyzed indium insertion into alkyl iodides and their synthetic utilities in cross-coupling reactions
A catalytic amount of cesium carbonate (10?mol%) was found to be capable of effectively catalyzing the insertion of indium powder into alkyl iodides. The thus-generated alkyl indium reagents could readily undergo palladium-catalyzed cross-coupling reactions with a wide variety of aryl halides, showing compatibility to a range of important functional groups.
Feng, Xue-Xin,Wu, Zhen,Wang, Qing-Dong,Chen, Bing-Zhi,Rao, Weidong,Yang, Jin-Ming,Shen, Zhi-Liang
(2019/07/31)

One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp2-Sp3 Cross-Coupling
A one-pot electrochemical nickel-catalyzed decarboxylative sp2-sp3 cross-coupling reaction has been developed using redox-active esters prepared in situ from alkyl carboxylates and N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (PITU). This undivided cell one-pot method enables C-C bond formation using inexpensive, benchtop-stable reagents with isolated yields up to 95% with good functional group tolerance, which includes nitrile, ketone, ester, alkene and selectivity over other aromatic halogens.
Koyanagi, Takaoki,Herath, Ananda,Chong, Ashley,Ratnikov, Maxim,Valiere, Andrew,Chang, Jim,Molteni, Valentina,Loren, Jon
p. 816 - 820
(2019/01/30)

Hetero-bifunctional catalyst manipulates carbonyl and alkynyl reductions of conjugated alkynones in an aqueous medium
Selective manipulation of carbonyl and alkynyl reductions in conjugated alkynones and controllable multi-step organic transformations are particularly attractive in green catalysis. In this study, using yolk-shell-structured silica, we design a mesoporous silica-supported active site-isolated bifunctional catalyst with Pd/C species on the yolk encapsulated by chiral Ru(ii)/diamine species in a silica shell. Structural analyses determine well-defined chiral single-site Ru(ii)/diamine species anchored in the nanochannels of silica shells, whereas electron microscopy characterizations disclose the uniformly distributed yolk-shell-structured morphology. As a dual reductive catalyst, it enables selective and successive carbonyl and alkynyl reductions of conjugated alkynones via a controllable catalysis sequence. The cascade reaction initially goes through Ru-catalyzed asymmetric transfer hydrogenation followed by a Pd/C-catalyzed reduction process to afford various chiral aromatic alcohols in high yields with up to 99% enantioselectivity in an aqueous medium. Furthermore, the designed functionalities of the catalyst including ethylene-bridged hydrophobicity, uniformly dispersed morphology, and dual acitve centers make integrated contribution to its catalytic performance.
Su, Yanchao,Chang, Fengwei,Jin, Ronghua,Liu, Rui,Liu, Guohua
p. 5397 - 5404
(2018/12/04)

Synthesis of Alkyl Indium Reagents by Using Unactivated Alkyl Chlorides and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions with Aryl Halides
An efficient method for the preparation of alkyl indium reagents by using unactivated and cheap alkyl chlorides as substrates in the presence of indium and LiI was developed. The thus-formed alkyl indium species effectively underwent palladium-catalyzed cross-coupling reactions with aryl halides with wide functional group tolerance.
Chen, Bing-Zhi,Zhi, Man-Ling,Wang, Chuang-Xin,Chu, Xue-Qiang,Shen, Zhi-Liang,Loh, Teck-Peng
supporting information
p. 1902 - 1905
(2018/04/16)

Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation
We developed a strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki-Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C-N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be installed. Preliminary studies suggest a NiI/NiIII catalytic cycle.
Basch, Corey H.,Liao, Jennie,Xu, Jianyu,Piane, Jacob J.,Watson, Mary P.
p. 5313 - 5316
(2017/04/27)

Plasma synthesis of oxidized graphene foam supporting Pd nanoparticles as a new catalyst for one-pot synthesis of dibenzyls
We have developed an environmentally-friendly method for the synthesis of Pd nanoparticle (Pd NPs) decorated different graphene supports, and the morphology and structure of the hybrids are characterized by transmission electron microscopy, X-ray diffraction, X-ray photoelectron spectroscopy and elemental mappings. Four hybrid materials based on graphene foam (GF), oxidized graphene foam (OGF), graphene oxide (GO) and reduced graphene oxide (RGO) have been used to catalyze Heck coupling reactions, and the effect of support on the activity of the hybrid material has been studied. Our results have revealed that Pd NP decorated OGF (Pd/OGF) is the most active catalyst, showing better performance than the commercial Pd/C catalyst. More importantly, the Pd/OGF catalyst has been successfully used for one-pot synthesis of dibenzyls with different aryl bromides and olefins, which has simplified the separation and purification process and realized a green organic synthesis process. This journal is
Ren, Liang,Yang, Fan,Wang, Chunxia,Li, Yongfeng,Liu, Hailing,Tu, Zhiqiang,Zhang, Liqiang,Liu, Zhichang,Gao, Jinsen,Xu, Chunming
p. 63048 - 63054
(2015/02/19)

Development of the direct Suzuki-Miyaura cross-coupling of primary B-alkyl MIDA-boronates and aryl bromides
The development of a palladium-catalyzed sp3-sp2 Suzuki-Miyaura cross-coupling of B-alkyl-N-methyliminodiacetyl (B-alkyl MIDA) boronates and (hetero)aryl bromides is reported. This transformation is tolerant of a variety of functional groups (F, NO2, CN, Cl, COCH3, and CHO). B-Alkyl MIDA boronates allow an efficient cross-coupling reaction directed toward the synthesis of unsymmetrical methylene diaryls as well as alkylated arenes in good to excellent yields.
St. Denis, Jeffrey D.,Scully, Conor C. G.,Lee, C. Frank,Yudin, Andrei K.
supporting information
p. 1338 - 1341
(2014/04/03)

Nickel-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature
A nickel-mediated intermolecular reductive cross-coupling reaction of unactivated alkyl bromides and aryl iodides at room temperature has been developed and successfully extended to less explored intramolecular versions and tandem cyclization-intermolecular cross-coupling. Highly stereoselective (or stereospecific) synthesis of linear-fused perhydrofuro[2,3-b]furan (pyran) and spiroketal skeletons allows rapid access to these useful building blocks, which would be potentially valuable in the synthesis of relevant natural products. A rational explanation for the formation of contiguous stereogenic centers is given. Copyright
Yan, Chang-Song,Peng, Yu,Xu, Xiao-Bo,Wang, Ya-Wen
supporting information; experimental part
p. 6039 - 6048
(2012/06/18)

Triplet-sensitized photoreactivity of a geminal diazidoalkane
Photolysis of 1 in chloroform yielded 2 as the major product and a small quantity of 3. Laser flash photolysis demonstrated that upon irradiation, the first excited triplet state of the ketone (T1K) of 1 is formed and decayed to form radical 4, which has a λmax at 380 nm (t = 2 μs). Radical 4 expelled a nitrogen molecule to yield imine radical 5 (λmax at 300 nm). Density functional theory (DFT) calculations showed that the transition state barrier for the formation of 5 is approximately 4 kcal/mol. In comparison, photolysis of 1 in argon matrices resulted in triplet nitrene 6, which was further characterized with 15N and D isotope labeling and DFT calculations. Prolonged irradiation of 6 yields triplet imine nitrene 7.
Upul Ranaweera, Ranaweera A. A.,Sankaranarayanan, Jagadis,Casey, Lydia,Ault, Bruce S.,Gudmundsdottir, Anna D.
p. 8177 - 8188
(2011/12/22)

Direct synthesis of water-tolerant alkyl indium reagents and their application in palladium-catalyzed couplings with aryl halides
A direct result: Alkyl indium reagents are synthesized by the insertion of indium into alkyl halide mediated by CuCl. The synthetic utility of these reagents is demonstrated by their palladium-catalyzed coupling with aryl halides (see scheme). The reagents are compatible with various functional groups, and this makes the protocol generally useful in organic synthesis. DMA=N,N-dimethylacetamide, TBS=tert-butyldimethylsilyl.
Shen, Zhi-Liang,Goh, Kelvin Kau Kiat,Yang, Yong-Sheng,Lai, Yin-Chang,Wong, Colin Hong An,Cheong, Hao-Lun,Loh, Teck-Peng
supporting information; experimental part
p. 511 - 514
(2011/03/17)

Coordination and catalytic properties of a semihomologous Dppf congener, 1-(diphenylphosphino)-1′-[(diphenylphosphino)methyl]ferrocene
Alcohol Ph2PfcCH2OH (2, fc = ferrocene-1,1′- diyl) reacts smoothly with Ph2PH and Me3SiCl/NaI in acetonitrile to give 1-(diphenylphosphino)-1′-[(diphenylphosphino)methyl] ferrocene (1), a new ferrocene diphosphine that fills the obvious gap left between the well-studied 1,1′-bis(diphenylphosphino)ferrocene (dppf) and its bis-spaced analogue, 1,1′-bis[(diphenylphosphino)methyl]ferrocene. The P-oxidized alcohols Ph2P(E)fcCH2OH (E = O, 3; S, 4) behave similarly, yielding the corresponding semichalcogenides Ph 2P(E)fcCH2PPh2 (E = O, 5; S, 6). Exhaustive oxidations of 1 with hydrogen peroxide or elemental sulfur produce Ph 2P(E)fcCH2P(E)Ph2 (E = O, 7; S, 8), while similar oxidations of 5 and 6 afford the unsymmetric bis-chalcogenides Ph 2P(O)fcCH2P(S)Ph2 (9) and Ph 2P(S)fcCH2P(O)Ph2 (10), respectively. Compounds 1 and 3-10 were characterized by spectral methods, and the crystal structures of 3 and 8-10 were determined by single-crystal X-ray diffraction analysis. Compound 1 reacts with group 10 metal dichloride precursors to give the respective chelate complexes [MCl2(1-κ2P,P′)] (11, M = Ni; 12, M = Pd; and 13, M = Pt). The Ni complex is paramagnetic and tetrahedral; the Pd and Pt complexes are expectedly square-planar and diamagnetic. Crystal structures of 11-13 reveal less acute ligand bite angles (P-M-P′) than those observed in the analogous dppf complexes, the difference being considerably larger for the Ni complex than in the less flexible square-planar complexes. Similarly to dppf and fc(CH 2PPh2)2, ligand 1 reacts with [(L NC)PdCl]2 (LNC = [2-(dimethylamino)methyl] phenyl) to give a diphosphine-bridged complex, [(μ-1){(LNC)PdCl} 2] (14), whereas the reaction with the mononuclear precursor [(L NC)Pd(MeCN)2]ClO4 yields a mixture of isomeric bis-chelates [(LNC)Pd(1-κ2P,P′)]ClO 4 (15a,b). Catalytic tests in Pd-catalyzed Suzuki-Miyaura cross-coupling and in Pd-catalyzed cyanation of aryl halides with K 4[Fe(CN)6]?3H2O suggest that introduction of one methylene spacer group into the structure of dppf influences catalytic performance only marginally.
Stepnicka, Petr,Cisarova, Ivana,Schulz, Jiri
experimental part
p. 4393 - 4403
(2011/10/18)

Efficient heterogeneously palladium-catalysed synthesis of stilbenes and bibenzyls
An alternative heterogeneously palladium catalysed procedure for the synthesis of functional stilbenes and bibenzyls is reported. Starting from aryl bromides and using simple commercially available Pd/C catalyst at a low catalytic rate (1 mol%), stilbenes are obtained with 30-100% GC-yields and bibenzyls are produced in a one-pot fashion with 27-100% GC-yields. The procedure showed, however, some limitations when applied to strongly deactivated aryl bromides that could be in some extent overcome by using corresponding iodo derivatives.
Cusati, Giuseppe,Wedig, Anja,Djakovitch, Laurent
scheme or table
p. 77 - 81
(2010/04/23)

Palladium-catalyzed heck coupling-hydrogenation: Highly efficient one-pot synthesis of dibenzyls and alkyl phenyl esters
An efficient method for the synthesis of industrially important dibenzyls and alkyl phenyl esters via sequential Heck coupling and hydrogenation of the alkenyl double bond in one pot with a single recyclable catalyst under mild conditions has been realised. The catalyst was recovered by simple filteration and reused for several cycles with consistent activity.
Kantam, M. Lakshmi,Chakravarti, Rajashree,Chintareddy, Venkat Reddy,Sreedhar,Bhargava, Suresh
supporting information; experimental part
p. 2544 - 2550
(2009/08/14)

Transfer semihydrogenation of alkynes catalyzed by a zero-valent palladium N-heterocyclic carbene complex
(Chemical Equation Presented) Beyond Lindlar and without hydrogen: Transfer hydrogenation of internal alkynes catalyzed by a palladium(0) catalyst containing an N-heterocyclic carbene ligand gives Z alkenes without over-reduction to alkanes (see scheme). Contrary to most transfer hydrogenations, ketones are not reduced. As such, this is the first catalyst that shows excellent stereo- and chemo-selectivity for the semihydrogenation of alkynes without the need for hydrogen gas.
Hauwert, Peter,Maestri, Giovanni,Sprengers, Jeroen W.,Catellani, Marta,Elsevier, Cornelis J.
p. 3223 - 3226
(2008/12/23)

1-(4-acetylphenyl)-2-phenylethane from potassium 2-phenethyltrifluoroborate and 4-bromoacetophenone
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Molander, Gary A.,Petrillo, Daniel E.,Denmark, Scott E.,Eggertswyler, Christophe
p. 317 - 324
(2017/09/12)

Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids
Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.
Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
p. 3813 - 3818
(2007/10/03)

Cross-coupling reactions of primary alkylboronic acids with aryl triflates and aryl halides
The cross-coupling reactions of primary alkylboronic acids with aryl triflates and aryl halides has been successfully achieved using PdCl2(dppf)·CH2Cl2 in the presence of potassium carbonate to provide the corresponding Su
Molander, Gary A.,Yun, Chang-Soo
p. 1465 - 1470
(2007/10/03)

Cross-coupling reactions of potassium alkyltrifluoroborates with aryl and 1-alkenyl trifluoromethanesulfonates.
[figure: see text] The palladium-catalyzed coupling reaction of potassium alkyltrifluoroborates with aryl- or alkenyltriflates proceeds to afford the corresponding arenes or alkenes in high yield. The borates are all solids, stable in air, and thus can be stored on the shelf indefinitely. The cross coupling can be effected using PdCl2(dppf).CH2Cl2 as the catalyst in THF-H2O in the presence of Cs2CO3. A variety of functional groups can be tolerated within the borate and/or the triflate coupling partner.
Molander,Ito
p. 393 - 396
(2007/10/03)

Palladium-Catalyzed Cross-Coupling Reaction of Alkyltrifluorosilanes with Aryl Halides
A cross-coupling reaction of alkyltrifluorosilanes with aryl halides was achieved using a catalytic amount of tetrakis-(triphenylphosphine)palladium(0) and excess of tetrabutylammonium fluoride (TBAF) at 100°C with high chemoselectitvity. Functional groups like nitro, ketone carbonyl, and formyl tolerated the coupling conditions. Because potassium(18-crown-6) alkyltetrafluorosilicates also underwent a cross-coupling reaction in the presence of an additional molar amount of TBAF, the active species of the coupling reaction was assumed to be pentacoordinate silicates. TBAF in excess was considered to be required for trapping the tetrafluorosilane produced in the catalytic cycle of the cross-coupling reaction.
Matsuhashi, Hayao,Asai, Satoshi,Hirabayashi, Kazunori,Hatanaka, Yasuo,Mori, Atsunori,Hiyama, Tamejiro
p. 437 - 444
(2007/10/03)

Liquid Crystalline Asymmetric Bisphenyl-4,4'-bibenzyldicarboxylates and Polysiloxanes with Bisphenyl-4,4'-bibenzyldicarboxylat Components in the Side Chains, Synthesis and Characterization
Asymmetric bisphenyl bibenzyl-4,4'-dicarboxylates with an alkenyloxy- or the 10-undecenoylgroup in the p-position of one terminal benzene ring and the butyl-, an alkoxy- or the thiomethylgroup in the p-position of the other terminal benzene ring (12-14) are synthesized.The olefins 12-14 are added to a poly(methylhydrogensiloxane) 15 to give mesomorphic side chain polysiloxanes 16-18.Data of liquid crystalline properties of 12-14, 16-18 and precursors are discussed.
Boberg, Friedrich,Mueller, Enno,Reddig, Wolfram
p. 136 - 142
(2007/10/02)

Palladium catalyzed cross-coupling reaction of functionalized alkyltrifluorosilanes with aryl halides
A variety of alkyltrifluorosilanes were found to couple with aryl halides in the presence of Pd(PPh3)4 catalyst and tetrabutylammonium fluoride (TBAF) to give the corresponding cross-coupled products in moderate to good yields.
Matsuhashi, Hayao,Kuroboshi, Manabu,Hatanaka, Yasuo,Hiyama, Tamejiro
p. 6507 - 6510
(2007/10/02)

ELECTROPHILIC AROMATIC SUBSTITUTION IN ARENE-TRICARBONYL-CHROMIUM COMPLEXES
The Friedel-Crafts acetylation and acid-promoted H-D exchange in tricarbonyl-chromium complexes of some diaryls, naphthalene and toluene were studied. For biphenyl and diphenylmethane complexes an assistance in electrophilic substitution by neigdbouring Cr(CO)3 was revealed. A reaction mechanism is proposed, comprising a preliminary formation of a relatively stable intermediate by the attack of electrophilie on the chromium atom, followed by transfer into the key intermediate, in a rate determining step. The key intermediate is formed through an early transition state (resembling a ?-complex) thus differing from free arenes where a late transition state (resembling a ?-complex) is operating. These features explain striking differences observed in orientation effects of complexes compared to "free" arenes.
Rosca, Sinziana,Chiraleu, Filip,Rosca, Sorin I.
p. 693 - 705
(2007/10/03)

A wide range of organosilicon compounds couples with enol and aryl triflates in the presence of Pd catalyst and fluoride ion
Under the influence of tetrakis(triphenylphosphine)palladium and tetrabutylammonium fluoride, the title reaction took place with alkenyl, alkynyl, aryl, and alkylsilanes to give the corresponding coupled products in good yields with high chemoselectivity and stereospecificity.
Hatanaka, Yasuo,Hiyama, Tamejiro
p. 2719 - 2722
(2007/10/02)

Product Study of Some One-Electron Oxidations of Bibenzyl and 4-Ethylbibenzyl. Evidence against Carbon-Carbon Bond Cleavage of the Bibenzyl Radical Cation in Solution
The oxidations of bibenzyl (1) and (or) 4-ethylbibenzyl (2) have been investigated under a variety of conditions, all of which should involve the intermediacy of bibenzyl radical cations: (a) reaction with ceric ammonium nitrate (CAN) in AcOH or CH3CN-H2O; (b) anodic oxidation in AcOH -CH3CN or (CH3)2CO-H2O; (c) photochemical oxidation by CAN in CH3CN; (d) photochemical autoxidation catalyzed by 9,10-dicyanoanthracene or by CAN in CH3CN.Nearly exclusive formation of side chain substituted products is observed for the chemical and electrochemical oxidations when the reactions are carried out in AcOH, CH3CN or AcOH-CH3CN, whereas extensive formation of C-C bond cleavage products occurs in the same processes when aqueous solvents are used.In the photochemical reactions, autoxidation produces both cleavage and side chain substituted products, whereas only the latter forms in the CAN-induced reaction in the absence of dioxygen.Evidence based on product analysis suggests that in these reactions no significant C-C bond breaking takes place at the state of bibenzyl radical cation.Cleavage products, where observed, nearly certainly derive from first-formed side chain substitution products
Baciocchi, Enrico,Bartoli, Donatella,Rol, Cesare,Ruzziconi, Renzo,Sebastiani, Giovanni V.
p. 3587 - 3593
(2007/10/02)