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Search for "biaryl" in Full Text gives 138 result(s) in Beilstein Journal of Organic Chemistry.

A toolbox of molecular photoswitches to modulate the CXCR3 chemokine receptor with light

  • Xavier Gómez-Santacana,
  • Sabrina M. de Munnik,
  • Tamara A. M. Mocking,
  • Niels J. Hauwert,
  • Shanliang Sun,
  • Prashanna Vijayachandran,
  • Iwan J. P. de Esch,
  • Henry F. Vischer,
  • Maikel Wijtmans and
  • Rob Leurs

Beilstein J. Org. Chem. 2019, 15, 2509–2523, doi:10.3762/bjoc.15.244

Graphical Abstract
  • latter one. One of the main reasons is that an azobenzene has a relatively simple structure that can resemble various biaryl moieties of bioactive compounds: two aromatic rings linked with a bridge (e.g., amide, ether, alkane or alkyne) [8]. In the case of azobenzene the bridge is a diazene group (also
  • called azo group) and depending on the wavelength of illumination, a linear trans-isomer or a bent cis-isomer can be obtained [9]. If certain biaryl moieties are replaced by an azobenzene (i.e., azologization approach), there is a relatively good chance that one of the resulting photoisomers will have a
  • spatial disposition similar to the original biaryl unit and, therefore, a similar biological activity that might change upon isomerization of the azobenzene [8]. The second reason for the success of azobenzene in the photopharmacology field is the robust photoisomerization. It provides typically high
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Published 23 Oct 2019

Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids

  • Benedikt C. Melzer,
  • Alois Plodek and
  • Franz Bracher

Beilstein J. Org. Chem. 2019, 15, 2304–2310, doi:10.3762/bjoc.15.222

Graphical Abstract
  • 4,5-disubstituted benzo[c][2,7]naphthyridines utilizing ortho-directed ring metalation/biaryl cross-coupling strategies [9]. 4-Chlorobenzo[c][2,7]naphthyridine (9a) was conveniently converted into other 4-substituted benzo[c][2,7]naphthyridines by substitution reactions with nucleophiles (alcoholates
  • manner of a radical reaction [27][28][29]. Starting with alcohol 12b, a putative precursor of the alkaloid kuanoniamine A (3), the three described cyclization methodologies were tested starting directly from alcohol 12b as well as from ketone 21, obtained by oxidation of 12b. The intramolecular biaryl
  • -catalysed intramolecular tandem stannylation/biaryl coupling protocol gave the attempted pentacyclic products [32]. However, having the biaryls 20a and 20b prepared we intended to develop a new approach to pyrido[4,3,2-mn]acridines by an alternative intramolecular cyclization step. To reach that aim, the
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Published 26 Sep 2019

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

  • Xiaowei Li,
  • Xiaolin Shi,
  • Xiangqian Li and
  • Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

Graphical Abstract
  • trifluoromethylation of vinyl triflates and nonaflates (Scheme 65). A variety of trifluoromethylated cyclohexenes were obtained using a catalyst system, which was composed of Pd(dba)2 or [(allyl)PdCl]2 and the monodentate biaryl phosphine ligand t-BuXPhos. Also, TMSCF3 and KF were more suitable to the
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Published 23 Sep 2019

Steroid diversification by multicomponent reactions

  • Leslie Reguera,
  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

Graphical Abstract
  • with a biaryl ether diisocyanide and two equivalents of paraformaldehyde and a monoprotected diamine. After the initial macrocyclization, steroidal macrocycle 71 was deprotected by removal of the Cbz groups and subsequently submitted to a second multicomponent macrocyclization protocol – in this case
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Published 06 Jun 2019

Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions

  • Angélica de Fátima S. Barreto and
  • Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2019, 15, 906–930, doi:10.3762/bjoc.15.88

Graphical Abstract
  • to be used directly to obtain macrocycles of this complexity and size. The synthesis of macrocycles with up to 16 new bonds being formed simultaneously has been described (Scheme 22). The strategy was based on combining steroidal dicarboxylic acids 115 and biaryl ether diisocyanide 116 [38]. The
  • approach provided the synthesis of steroid-biaryl ether hybrid macrocycles 117 and 118 with up to 68 members by the MiBs strategy. Another representative example of MiBs is the synthesis of the biaryl ether-containing macrocycles 123a–f (Scheme 23) [39]. The synthetic strategy involved the mixing of three
  • products containing biaryl ether-cyclopeptoid macrocycles 127 and 128 (Scheme 24) [40]. The approach used involved diisocyanides 124 (representing a biaryl ether moiety) reacting with aliphatic diacid/diamine and amine/aldehyde, respectively, to generate the target macroheterocycles. Wessjohann and Rivera
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Published 15 Apr 2019

A diastereoselective approach to axially chiral biaryls via electrochemically enabled cyclization cascade

  • Hong Yan,
  • Zhong-Yi Mao,
  • Zhong-Wei Hou,
  • Jinshuai Song and
  • Hai-Chao Xu

Beilstein J. Org. Chem. 2019, 15, 795–800, doi:10.3762/bjoc.15.76

Graphical Abstract
  • the biaryls with good to excellent central-to-axial chirality transfer. Keywords: axial chirality; biaryl; electrochemistry; oxidation; radical; Introduction Axially chiral biaryls are prevalent in natural products, bioactive molecules and organocatalysts [1][2]. Among the many methods that have
  • imidazopyridine-based biaryl 3a in 68% yield with good diastereoselectivity (14:1 dr). Replacing the t-Bu group at the propargylic position with iPr (Table 1, entry 2) or on the phenyl ring with Ph (Table 1, entry 3) or OiPr (Table 1, entry 4) all resulted in low diastereoselectivity (2:1 to 3:1). The scope of
  • Me (3j). Pyridyl rings bearing multiple substituents were also tolerated (3k and 3l). The stereochemistry of the biaryl product was determined by obtaining an X-ray crystal structure of 3k. The t-Bu-substituted phenyl ring on the alkyne moiety containing an extra OMe (3m) or Me (3n and 3o) group was
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Published 28 Mar 2019

Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

  • Iteng Ng-Choi,
  • Àngel Oliveras,
  • Lidia Feliu and
  • Marta Planas

Beilstein J. Org. Chem. 2019, 15, 761–768, doi:10.3762/bjoc.15.72

Graphical Abstract
  • Iteng Ng-Choi Angel Oliveras Lidia Feliu Marta Planas LIPPSO, Departament de Química, University of Girona, Maria Aurèlia Capmany 69, Girona 17003, Spain 10.3762/bjoc.15.72 Abstract A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr
  • resulting biaryl monocyclic peptidyl resin leading to the formation of the expected biaryl bicyclic peptide. This study provides the first solid-phase synthesis of this type of bicyclic compounds being amenable to prepare a diversity of synthetic or natural biaryl bicyclic peptides. Keywords: borylation
  • amino acids [11]. Cyclic peptides containing biaryl linkages constitute attractive targets. On the one hand, a wide range of biaryl natural products have been reported to display interesting biological properties, such as biphenomycins, arylomycins and glycopeptide antibiotics [4]. On the other hand
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Published 22 Mar 2019

Silanediol versus chlorosilanol: hydrolyses and hydrogen-bonding catalyses with fenchole-based silanes

  • Falco Fox,
  • Jörg M. Neudörfl and
  • Bernd Goldfuss

Beilstein J. Org. Chem. 2019, 15, 167–186, doi:10.3762/bjoc.15.17

Graphical Abstract
  • ). For 8ax the OH group is parallel situated to the biaryl axis. For 8eq the OH group is orthogonal oriented to the biaryl axis. The fenchyl groups are abbreviated with (*) for more clarity. Computed hydrolyses of BIFOXSiCl2 (7) to BIFOXSiCl(OH) 8ax and BIFOXSiCl(OH) 8eq and subsequent computed
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Published 18 Jan 2019

A simple and effective preparation of quercetin pentamethyl ether from quercetin

  • Jin Tatsuzaki,
  • Tomohiko Ohwada,
  • Yuko Otani,
  • Reiko Inagi and
  • Tsutomu Ishikawa

Beilstein J. Org. Chem. 2018, 14, 3112–3121, doi:10.3762/bjoc.14.291

Graphical Abstract
  • position shows the lowest reactivity, while the OH group at 7 position shows the highest reactivity. In the cases of anions 2B, all the corresponding anions 3'-anion 2B, 4'-anion 2B, 5-anion 2B, 7-anion 2B tended to take planar overall structures, that is, the biaryl dihedral angles (3–2–1'–2') were
  • reduced from that of the neural species (2B: −43.8°). In particular, 4'-anion 2B and 5-anion 2B are affected by conjugation between the chromenone moiety and the phenyl group (biaryl dihedral angle: −29.6° in 4'-anion 2B; −29.6° in 5-anion 2B). Change of proton affinity during the methylation reaction
  • '-tetramethylquercetin (4, conformation 4A). Conformation 4A has a structure in which the phenyl group is rotated due to the OMe group at the 3 position (the biaryl dihedral angle is +28.2°), and upon ionization of the OH at 5 position to the oxyanion, the planarity was not significantly restored. This may increase the
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Published 28 Dec 2018

Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections

  • Matthew B. Calvert,
  • Varsha R. Jumde and
  • Alexander Titz

Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239

Graphical Abstract
  • signal molecules and mimic their structures. The PQS system of P. aeruginosa is particularly attractive and can be considered as a pathogen specific target. The biosynthesis of the PQS signal 23 involves a set of biosynthetic enzymes PqsABCDEH and its autocatalytic receptor PqsR (MvfR). Biaryl methanols
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Published 11 Oct 2018

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

  • Sambasivarao Kotha,
  • Milind Meshram and
  • Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

Graphical Abstract
  • a CM in an efficient manner. Biaryl derivatives In view of the interesting properties of biaryl derivatives, we have identified a three-step sequence, which involve cross-enyne metathesis (CEM), DA reaction followed by SM coupling [46]. To this end, acetylene derivatives 96a,b were subjected to CEM
  • DDQ to give biaryl products 99a,b. Further, aryl halides 99a,b were subjected to SM coupling by employing various boronic acids (e.g., 4-formylphenylboronic acid (100) to produce biaryl derivative 101 (80% from 99a and 74% from 99b). Very recently, Suresh Babu and co-workers [47] demonstrated a new
  • coupling approach to Z-stilbene derivative 85. Synthesis of substituted trans-stilbene derivatives via SM coupling and RCM. Synthesis of biaryl derivatives via sequential EM, DA followed by SM coupling. Synthesis of the dibenzocyclooctadiene core of schisandrene. Synthesis of cyclophane 115 via SM coupling
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Published 21 Sep 2018

Some mechanistic aspects regarding the Suzuki–Miyaura reaction between selected ortho-substituted phenylboronic acids and 3,4,5-tribromo-2,6-dimethylpyridine

  • Piotr Pomarański,
  • Piotr Roszkowski,
  • Jan K. Maurin,
  • Armand Budzianowski and
  • Zbigniew Czarnocki

Beilstein J. Org. Chem. 2018, 14, 2384–2393, doi:10.3762/bjoc.14.214

Graphical Abstract
  • , Tanaka presented an atropselective synthesis of axially chiral all-benzenoid biaryls by gold-catalysed intramolecular hydroarylation of alkynones to give the desired atropisomeric product with a good ee value of 70% [26]. Conventional approaches to the synthesis of biaryl compounds having axial chirality
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Published 11 Sep 2018

Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

  • Siva Sankar Murthy Bandaru,
  • Darinka Dzubiel,
  • Heiko Ihmels,
  • Mohebodin Karbasiyoun,
  • Mohamed M. A. Mahmoud and
  • Carola Schulzke

Beilstein J. Org. Chem. 2018, 14, 1871–1884, doi:10.3762/bjoc.14.161

Graphical Abstract
  • ]quinolizinium derivatives have to be optimized [34][35]. Accordingly, we extended our studies to improve the conditions of the Suzuki–Miyaura coupling towards biaryl-type benzo[b]quinolizinium derivatives 1a–d (Figure 1), namely to apply the alternative base-free Suzuki–Miyaura coupling reaction [39][40][41][42
  • shift in CHCl3. This effect is presumably caused by a charge shift (CS) or, more likely, by a charge transfer (CT) in the excited state from the electron-donating aryl unit to the excited quinolizinium (Scheme 3) [57], which has been proposed also to take place in structurally resembling excited biaryl
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Published 23 Jul 2018

Water-soluble SNS cationic palladium(II) complexes and their Suzuki–Miyaura cross-coupling reactions in aqueous medium

  • Alphonse Fiebor,
  • Richard Tia,
  • Banothile C. E. Makhubela and
  • Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1859–1870, doi:10.3762/bjoc.14.160

Graphical Abstract
  • equiv) led to the formation of the biaryl 23a in 92% yield (Table 2, entry 1). The colour of the reaction mixture remained yellow. The use of solvents other than water gave inferior yields (Table 2, entries 2 and 3) which could be attributed to the high hydrophilicity of the pincer complex 17a. Several
  • bases including pyridine, Et3N, KOH, K2CO3 and Cs2CO3 were then evaluated. All except Et3N provided the expected biaryl 23a in comparable and excellent yields (Table 2, entries 4–8). The poor performance of Et3N as base in the reaction could be due to its low water solubility. KOH as a common laboratory
  • activity of 20a was investigated in the Suzuki–Miyaura coupling reaction of 4-bromoanisole (21a) and phenylboronic acid (22a) as a proof of concept. As expected, it catalysed the reaction and provided biaryl 23a in moderate yield demonstrating the potential of such complexes in coupling reactions (Scheme 4
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Published 23 Jul 2018

A survey of chiral hypervalent iodine reagents in asymmetric synthesis

  • Soumen Ghosh,
  • Suman Pradhan and
  • Indranil Chatterjee

Beilstein J. Org. Chem. 2018, 14, 1244–1262, doi:10.3762/bjoc.14.107

Graphical Abstract
  • purpose various chiral iodine reagents were synthesized having an axially chiral biaryl backbone. In this part, we mainly focused on the transformations using chiral iodine reagents instead of achiral iodine reagents in a combination with other chiral sources [61]. More than one century after Pribam
  • for the alkynylation of β-ketoesters [76]. Pouységu and Quideau et al. prepared new axially chiral biaryl I(III) reagents 18 assembled with alkynyl ligands. They were able to achieve alkynylation of β-ketoesters 114 as well as dearomative alkynylation of phenolic derivatives 118 to obtain derivatives
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Published 30 May 2018

Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry

  • Katharina Hiebler,
  • Georg J. Lichtenegger,
  • Manuel C. Maier,
  • Eun Sung Park,
  • Renie Gonzales-Groom,
  • Bernard P. Binks and
  • Heidrun Gruber-Woelfler

Beilstein J. Org. Chem. 2018, 14, 648–658, doi:10.3762/bjoc.14.52

Graphical Abstract
  • ) [31][32][33][34][35]. A preliminary scheme of the planned synthetic route is shown in Figure 1. As can be seen, the key step of our processes is the formation of the biaryl unit via a Suzuki–Miyaura cross-coupling reaction. To provide solid Pd catalysts with a high potential for the planned approaches
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Published 19 Mar 2018

Diels–Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts

  • Huangguan Chen,
  • Jianwei Han and
  • Limin Wang

Beilstein J. Org. Chem. 2018, 14, 354–363, doi:10.3762/bjoc.14.23

Graphical Abstract
  • were well tolerated with N-methyl and N-phenyl groups (Scheme 1a) [7]. Ackermann et al. employed a 2,5-dimethylpyrrole derivative as substrate to deliver double arylated products at 3,4-positions of the pyrrole ring (Scheme 1b) [8]. Recently, the research group of Kita documented an oxidative biaryl
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Published 06 Feb 2018

One-pot sequential synthesis of tetrasubstituted thiophenes via sulfur ylide-like intermediates

  • Jun Ki Kim,
  • Hwan Jung Lim,
  • Kyung Chae Jeong and
  • Seong Jun Park

Beilstein J. Org. Chem. 2018, 14, 243–252, doi:10.3762/bjoc.14.16

Graphical Abstract
  • ][40][41][42][43]. Consequently, we are fascinated with thienyl–pyridyl ring systems [43] and have explored facile synthetic procedures to facilitate their production. For the synthesis of heterocyclic–heterocyclic biaryl compounds, numerous studies have been carried out to develop efficient catalytic
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Published 26 Jan 2018

CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na

  • Hélène Guyon,
  • Hélène Chachignon and
  • Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

Graphical Abstract
  • . In the case of unsymmetrical biaryl substrates, mixtures of regioisomers at C4 and C5 were obtained (Scheme 48). In the reaction mechanism, PIFA played a dual role in the activation of the arene via a π-complex and in the generation of the CF3 radical from CF3SO2Na. More recently, Maruoka and co
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Published 19 Dec 2017

Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes

  • Takeshi Fujita,
  • Ryo Kinoshita,
  • Tsuyoshi Takanohashi,
  • Naoto Suzuki and
  • Junji Ichikawa

Beilstein J. Org. Chem. 2017, 13, 2682–2689, doi:10.3762/bjoc.13.266

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  • Takeshi Fujita Ryo Kinoshita Tsuyoshi Takanohashi Naoto Suzuki Junji Ichikawa Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan 10.3762/bjoc.13.266 Abstract 1,1-Difluoro-1-alkenes bearing a biaryl-2-yl group effectively underwent
  • intermediates [23][24][25][26][27]. Thus, we examined and eventually achieved complete control over the regioselectivity at the carbon atoms in β-position as well as those in α-position to the fluorine in the intramolecular Friedel–Crafts-type iodoarylation of 1,1-difluoro-1-alkenes bearing a biaryl group
  • probability. ORTEP diagram of 6a with 50% ellipsoid probability. Intramolecular site-selective iodoarylation of 1,1-difluoro-1-alkenes bearing a biaryl group. Mechanism for formation of 3a. Transformation of a CF2I group of 2a into a CHF2 group. Construction of seven-membered carbocycles via iodoarylation of
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Published 14 Dec 2017

A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines

  • Benedikt C. Melzer and
  • Franz Bracher

Beilstein J. Org. Chem. 2017, 13, 1564–1571, doi:10.3762/bjoc.13.156

Graphical Abstract
  • bianfugecine (6) were isolated from Menispermum dauricum DC, among a few other plants [1][7][8]. A number of approaches to the oxoaporphine ring system has been published, typically involving the synthesis of 1-benzyl/1-benzoylisoquinoline intermediates, followed by cyclization under intramolecular biaryl
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Published 08 Aug 2017

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

  • Kohei Yamada,
  • Naoto Kamimura and
  • Munetaka Kunishima

Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146

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  • , Jin and co-workers reported that Ni-catalyzed Suzuki–Miyaura coupling between triazinyloxybenzene and arylboronic acids affords the corresponding biaryl compounds [24][25][26][27][28][29][30][31][32][33]. In this context, we envisioned application of this Suzuki–Miyaura coupling to a 5-(triazinyloxy
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Published 27 Jul 2017

Transition-metal-catalyzed synthesis of phenols and aryl thiols

  • Yajun Liu,
  • Shasha Liu and
  • Yan Xiao

Beilstein J. Org. Chem. 2017, 13, 589–611, doi:10.3762/bjoc.13.58

Graphical Abstract
  • ]. Rao and co-workers found that both biaryl ketone and aryl alkyl ketones could be regioselectively hydroxylated in satisfying yields. The reaction proceeded in TFA/TFAA in the presence of Pd(OAc)2 as catalyst and several type of oxidants including selectfluor, PhI(OAc)2 and K2S2O8, respectively (Scheme
  • with aryl iodides at 90 °C in the presence of CuI as catalyst to afford biaryl disulfides and polysulfides, which could be further converted to aryl thiols through a followed reduction using NaBH4 or PPh3 (Scheme 59) [103]. A wide range of functional groups including methoxy, hydroxy, acyl, carboxy
  • hydroxylation of benzimidazolylarenes. Dioxane mediated hydroxylation of 2-heteroarylarenes. Hydroxylation of oxime methyl ester. CN-directed meta-hydroxylation. Pd(OAc)2-catalyzed hydroxylation of benzoic acids. Pd(OAc)2-catalyzed hydroxylation of biaryl or aryl alkyl ketones. Pd(OAc)2 and Pd(TFA)2 catalyzed
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Published 23 Mar 2017

Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

  • Yi Lai,
  • Zhijian Zong,
  • Yujie Tang,
  • Weimin Mo,
  • Nan Sun,
  • Baoxiang Hu,
  • Zhenlu Shen,
  • Liqun Jin,
  • Wen-hua Sun and
  • Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 213–221, doi:10.3762/bjoc.13.24

Graphical Abstract
  • (50 mL), the resulted solution was concentrated under vacuum and the desired biaryl was isolated by column chromatography. The steric geometry-constrained iminopyridyl–palladium complexes. ORTEP drawing of Pd2 with thermal ellipsoids at 30% probability level. Hydrogen atoms and the solvent CH2Cl2 have
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Published 03 Feb 2017

Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I)

  • Sem Raj Tamang and
  • James D. Hoefelmeyer

Beilstein J. Org. Chem. 2016, 12, 2757–2762, doi:10.3762/bjoc.12.272

Graphical Abstract
  • SET mechanism [57], electron donation to ArI leads to a short-lived radical anion ArI•− that decomposes to I− and Ar•. The Ar radical undergoes homolytic aromatic substitution with benzene to form a biaryl radical, and deprotonation gives a biaryl radical anion that transfers one electron to ArI to
  • ]. Thus, t-BuO− substitutes the halogen ligand on 2, followed by deprotonation–metalation of benzene, followed by oxidative addition of the arylhalide, and finally reductive elimination of the biaryl. The molecule 2 may be uniquely suited for this pathway. The electron-rich Cu(I) in the (L-Z)Cu(OR
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Published 15 Dec 2016
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