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January

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Bingli's paper

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Copper(I)-catalyzed asymmetric monoborylation of 1,3-dienes has been developed. We describe the production of either optically active homoallyl- or allylboronates with high regio- and enantioselectivity (88−97% ee) through monoborylation of 1,3-dienes. The reaction with 1,3-cyclohexadiene derivatives afforded the corresponding enantioenriched homoallyboronates. By simply changing the reaction conditions, a drastic change of product preference between homoallyl- and allylboronates was found in the reaction of 1,3-cyclopentadiene and 1,3-cycloheptadiene.

Guillaume's paper

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A highly active and enantioselective titanium-catalyzed cyanation of imines at room temperature is described. The catalyst used is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields in 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as benzyl, benzhydryl, Boc, and PMP are tolerated.


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Tori's Paper

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Vickys Paper

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DOI: 10.1021/ja910083q

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February

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Yoyo's paper

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Helena's paper

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Kinetic resolution of strained three-membered rings has proven broadly useful for the generation of enantiopure organic intermediates. Herein we demonstrate a complementary approach whereby a single catalyst transforms a racemic mixture of aziridines to a pair of regioisomeric products, each in good yield with exceptionally high enantioselectivity. Specifically, the dimeric yttrium salen catalyst accelerates the ring opening of aliphatic aziridines by trimethylsilylazide, inducing nucleophilic attack at the primary position of one enantiomer and the secondary position of the other. Both rate and selectivity are highly sensitive to the catalyst structure.

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Sarah's paper

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Andy's Paper

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Creating CF bonds: A novel electrophilic fluorination of aryl and heteroaryl Grignard reagents has been discovered and was used for the efficient synthesis of various aryl fluoride derivatives (see picture; THF=tetrahydrofuran).
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Shigeyuki Yamada, Dr., Andrei Gavryushin, Dr., Paul Knochel, Prof. Dr.
Give me an F: Electrophilic fluorination of various aromatic and heteroaromatic Grignard reagents is smoothly performed with (PhSO2)2NF as fluorinating agent in a 4:1 mixture of CH2Cl2/perfluorodecalin (see scheme). This solvent system allows minimization of most side reactions.

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Bingli's Paper

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Heteroarenes are important structural moieties in many chemical industry fields. A highly efficient Pd/Cu-catalyzed C−H arylation method for a range of heterocycles has been discovered. It was found that the key to the success of this transformation is a combination of a palladium catalyst and a well-defined copper cocatalyst. The efficiency and low loadings of catalyst (0.25 mol %) and cocatalyst (1 mol %) together with the mild reaction conditions demonstrate this method to be practically useful and mechanistically interesting.

Guillaume's Paper

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Cationic organic intermediates participate in a wide variety of useful synthetic transformations, but their high reactivity can render selectivity in competing pathways difficult to control. Here, we describe a strategy for inducing enantioselectivity in reactions of protio-iminium ions, wherein a chiral catalyst interacts with the highly reactive intermediate through a network of noncovalent interactions. This interaction leads to an attenuation of the reactivity of the iminium ion and allows high enantioselectivity in cycloadditions with electron-rich alkenes (the Povarov reaction). A detailed experimental and computational analysis of this catalyst system has revealed the precise nature of the catalyst-substrate interactions and the likely basis for enantioinduction.

March

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Andy's Paper

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Sarah's paper

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Vickys Paper

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Fede's paper

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Mahesh's Paper

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Angew. Chem. Int. Ed. 2010, 49, 772-775
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In this paper, Manabe et al. presents DHTP (dihydroxyterphenylphosphine) ligands as a new class of ligands for palladium catalysed highly ortho-selective cross-coupling of Grignard reagent with dihaloarenes. The rationale behind the design of these ligands has been well presented with a number of examples involving cross-coupling of arylmagnesium bromide with 2,4-dibromophenol, 2,5-dibromophenol, 2,4-dibromoaniline, 1,6-dibromonaphth-1-ol, 2-chloro-4-bromophenol, affording ortho-cross coupled product exclusively in all cases. This remarkable ortho-selective cross-coupling can be achieved by employing as less than 1 mol% of Pd2(dba)3 and 2.4 mol% of the DHTP ligand at room temperature in about 2-5 h. It is expected that this ligand will soon find application in several metal catalysed site-selective cross-coupling reactions to build drug frameworks and synthetic intermediates.   

April

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Bingli's Paper

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Mahesh's Paper

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Tobias Blumke, Yi-Hung Chen, Zhihua Peng and Paul Knochel*

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The authors have demonstrated the utility of this protocol to generate a range of aryl and alkenyl organoaluminium reagents containing various functionalities.  Further, these resulting new organoaluminium reagents undergo smooth Pd-catalysed cross-coupling and acylation reactions, as well as copper-catalysed allylic substitutions, affording various interesting products for pharmaceutical and material science applications.

May

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Fede's paper

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Helena's paper

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Jimmy's paper

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Unsymmetrical diarylalkynes are accessible by a one-pot procedure from two different aryl halides and (trimethylsilyl)acetylene. The three-component coupling is initialized by a Pd/Cu-catalyzed Sonogashira coupling of an aryl halide with (trimethylsilyl)acetylene. After subsequent desilylation of the formed aryl(trimethylsilyl)acetylene with aqueous potassium hydroxide, a second Sonogashira coupling with an aryl iodide that does not require any additional Pd/Cu-catalyst gives access to an unsymmetrical diarylalkyne.


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Ola's Paper

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Chem. Commun., 2010, 46, 3025 - 3027, DOI: 10.1039/c002825h

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Helena's paper

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July

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Jimmy's paper

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Mahesh's Paper

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Vicky's Paper

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DOI:10.1002/anie.201002591
The titled reaction proceeds in the presence of a thiolate-bridged diruthenium complex (2) and a secondary amine (1) to give the corresponding propargylic alkylated products in excellent yields as a mixture of two diastereoisomers, each with high enantioselectivity. The two catalysts activate propargylic alcohols and aldehydes, respectively, and cooperatively promote the enantioselective reaction.


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Enzymes are a continuing source of inspiration for the design of new chemical reactions that proceed with efficiency, high selectivity and minimal waste. In many biochemical processes, different catalytic species, such as Lewis acids and bases, are involved in precisely orchestrated interactions to activate reactants simultaneously or sequentially. This type of ‘cooperative catalysis’, in which two or more catalytic cycles operate concurrently to achieve one overall transformation, has great potential in enhancing known reactivity and driving the development of new chemical reactions with high value. In this disclosure, a cooperative N-heterocyclic carbene/Lewis acid catalytic system promotes the addition of homoenolate equivalents to hydrazones, generating highly substituted γ-lactams in moderate to good yields and with high levels of diastereo- and enantioselectivity.

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Mahesh's Paper

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Wenjun Tang*, Andrew G. Capacci, Xudong Wei, Wenjie Li, Andre White, Nitinchandra  D. Patel, Jolaine Savoie, Joe J. Gao, Sonia Rodriguez, Bo Qu, Nizar Haddad, Bruce Z. Lu, Dhileepkumar Krishnamurthy, Nathan K. Yee, Chris H. Senanayake
 
In this paper, Tang and co-workers report a new class of biaryl monophosphorus ligands (e.g. BI-DMIE) containing a 2,3-dihydrobenzo[d][1,3]oxaphosphole framework that are highly effective for the palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of a wide range of substrates.  Notable feature of this ligand is its remarkable ability to cross couple extremely hindered aryl boronic acids with hindered aryl chlorides and bromides and vice versa which otherwise could not be achieved by some of the efficient and widely used ligands at the present such as S-Phos, X-Phos, Ru-Phos, PCy3, PtBu3, etc. The ability to achieve this difficult transformation will make BI-DIME a more general ligand to construct tri-ortho-subsituted biaryls via Suzuki-Miyaura cross-coupling method. 

i crack an egg on your head Though this new ligand currently suffers from a long synthetic route, when commercialized will be widely used in the academic R&D laboratories, pharmaceutical, agro-chemical and allied industries.  There is no doubt this paper will attract greater attention among chemists in the near future.

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Mahesh's Paper

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download stick cricket for nokia 2700 classic Abstract: Despite the widespread use of axially chiral, or atropisomeric, biaryl ligands in modern synthesis and the occurrence of numerous natural products exhibiting axial chirality, few catalytic methods have emerged for the direct asymmetric preparation of this compound class. This paper reports a tripeptide-derived small-molecule catalyst for the dynamic kinetic resolution of racemic biaryl substrates. The reaction proceeds via an atropisomer-selective electrophilic aromatic substitution reaction using simple bromination reagents. The result is an enantioselective synthesis that delivers chiral nonracemic biaryl compounds with excellent optical purity and good isolated chemical yields (in most cases a >95:5 enantiomer ratio and isolated yields of 65 to 87%). A mechanistic model is advanced that accounts for the basis of selectivity observed.

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Guillaume's paper

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DOI: 10.1021/ol101789g

1 9 16 to millimeters The enantioselective synthesis of (Z)-1,2-anti-2,5-anti-triol monosilyl ethers via a two-step sequence involving olefin cross-metathesis of β-alkoxyallylboronate and subsequent allylboration of the derived bisboryl intermediate provides triol monoethers with good to excellent diastereoselectivity.

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DOI: 10.1002/anie.201003755

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October

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Mahesh's Paper

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shea butter for cracked nipples Orthogonally functionalized, programmable biaryl templates have been synthesized utilizing aryl acetylenic stannanes and oxygenated dienes in a cycloaddition/cycloreversion strategy. Sequential functionalization of each of the four ortho positions has been demonstrated. Subsequent resolution of a representative anilino phenol has been accomplished. Additionally, a highly active anhydrous, boroxine-based Suzuki coupling protocol has been developed for conversion of unreactive aryl chlorides.


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Guillaume's paper

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Department of Chemistry, The Scripps Research Institute

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Jimmy's paper

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Bingli's paper

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Lucy's Paper

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Abstract - For the first time, we have modified phenylalanine peptides by the Suzuki-Miyaura coupling reaction which may be useful in developing combinatorial libraries of peptidomimetics.

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Andy's Paper

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Lucy's Paper

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crack the spine literary magazine We report the first examples of a “BN-fused” indole, and we demonstrate that this new family of unnatural indole derivatives undergoes electrophilic aromatic substitution (EAS) reactions with the same regioselectivity as its organic analogue. Competition experiments reveal that N-t-Bu-BN-indole is more nucleophilic in EAS reactions than its carbonaceous counterpart. X-ray structural analysis between BN indole and classic indole highlights significant differences in bond distances, in particular for bonds associated with the boron atom.

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Helena's paper

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Mahesh's Papers

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Bis-Terminal Hydroxy Polyethers as All-Purpose, Multifunctional Organic Promoters: A Mechanistic Investigation and Applications

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Achiral polyether derivatives have been shown to dramatically accelerate SN2 reactions by the simultaneous activation of both the nucleophile (KF) and electrophile (sulfonate; see picture). By using chiral variants as catalysts, the desilylative kinetic resolution of the silyl ethers of racemic secondary alcohols has been achieved. Density functional calculations provide detailed insight into the modes of action of this type of organic promoter.

December

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Bingli's paper

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Helena's paper

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Angew. Chem. Int. Ed., 2010, 49, 1-5

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