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Tuesday, October 25, 2011

Participation of Carbonyl Oxygen in Carbon–Carboxylate Bond-Forming Reductive Elimination from Palladium - Organometallics (ACS Publications)

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Melanie S. Sanford, Organometallics, 2011DOI: 10.1021/om200677y

Palladium(II) Agostic Complex: Exchange of Aryl–Pd and Alkyl–Pd Bonds

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Organometallics, 2011, DOI: 10.1021/om200451v

NiCl2(PMe3)2-Catalyzed Borylation of Aryl Chlorides

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2011, OL, DOI: 10.1021/ol202267t

Oxidative C–H Homodimerization of Phenylacetamides

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Michael F. Greaney,  2011, OL, DOI: 10.1021/ol202212f

Palladium(II)-Catalyzed Dehydrogenative Alkenylation of Cyclic Enaminones via the Fujiwara–Moritani Reaction

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2011, OL, DOI: 10.1021/ol202677g

TEMPO Oxoammonium Salt-Mediated Dehydrogenative Povarov/Oxidation Tandem Reaction of N-Alkyl Anilines

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OL, 2011, DOI: 10.1021/ol202552y

Cu(II) Catalyzed Imine C–H Functionalization Leading to Synthesis of 2,5-Substituted 1,3,4-Oxadiazoles

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OL, 2011, DOI: 10.1021/ol202409r

Sequential and One-Pot Reactions of Phenols with Bromoalkynes for the Synthesis of (Z)-2-Bromovinyl Phenyl Ethers and Benzo[b]furans

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OL, 2011, DOI: 10.1021/ol202383z

Oxidative Cyclization of 2-Aryl-3-arylamino-2-alkenenitriles to N-Arylindole-3-carbonitriles Mediated by NXS/Zn(OAc)2

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Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes

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Masahiro Miura, 2011, JOC, DOI: 10.1021/jo201923d

Palladium-Catalyzed Intramolecular C–H Activation/C–C Bond Formation: A Straightforward Synthesis of Phenanthridines

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JOC, 2011, DOI: 10.1021/jo2017108

Palladium-Catalyzed Coupling of Arene C–H Bonds with Methyl- and Arylboron Reagents Assisted by the Removable 2-Pyridylsulfinyl Group

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J. Org. Chem, 2011DOI: 10.1021/jo2018137

Innate and Guided C–H Functionalization Logic

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 Phil S. Baran, Acc. Chem. Res., 2011,DOI: 10.1021/ar200194b

Rare-Earth-Catalyzed C–H Bond Addition of Pyridines to Olefins

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Zhaomin Hou, 2011, JACS, DOI: 10.1021/ja208129t

Nickel-Catalyzed Dehydrogenative [4 + 2] Cycloaddition of 1,3-Dienes with Nitriles

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Sensuke Ogoshi, JACS, 2011, DOI: 10.1021/ja208162w

C–H Bond Activation at Palladium(IV) Centers

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Melanie S. Sanford, JACS, 2011, DOI: 10.1021/ja2051099

Ligand-Accelerated Cross-Coupling of C(sp2)–H Bonds with Arylboron Reagents

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Jin-Quan Yu, JACS, 2011, DOI: 10.1021/ja203978r

Thursday, October 20, 2011

Cobalt-Catalyzed, Room-Temperature Addition of Aromatic Imines to Alkynes via Directed C–H Bond Activation

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Naohiko Yoshikai, JACS 2011, DOI: 10.1021/ja2047073

Synthesis of Functionalized 1H-Indenes via Copper-Catalyzed Arylative Cyclization of Arylalkynes with Aromatic Sulfonyl Chlorides

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Eiichi Nakamura, JACS 2011, DOI: 10.1021/ja209300c

Synthesis of Catechols from Phenols via Pd-Catalyzed Silanol-Directed C–H Oxygenation

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A silanol-directed, Pd-catalyzed C–H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the catechol product.

Vladimir Gevorgyan, JACS 2011, DOI: 10.1021/ja208572v

Concentration of Acids and Bases

Properties of various acids and bases
The data in the following table (except MW) is approximate and should only be used as an estimate. Concentrations change upon exposure to air.
Reagent
Formula
Molecular Weight (g/mol)
Specific gravity
Normality of conc. reagent
Weight %
V (mL)*
Acetic acid (glacial)
CH3CO2H
60.05
1.05
17.45
99.8
57.3
Ammonium hydroxide
NH4OH
35.05
0.90
14.53
56.6
Ethylene diamine
C2H4(NH2)2
60.10
0.899
15.0
100
66.7
Formic acid
HCO2H
46.03
1.20
23.6
90.5
42.5
Hydrazine
N2H4
32.05
1.01
30.0
95
33.3
Hydriodic acid
HI
127.91
1.70
7.6
57
132
Hydrobromic acid
HBr
80.92
1.49
8.84
48
113
Hydrochloric acid
HCl
36.46
1.19
12.1
37.2
82.5
Hydrofluoric acid
HF
20.0
1.18
28.9
49.0
34.5
Nitric acid
HNO3
63.01
1.42
15.9
70.4
63
Perchloric acid
HClO4
100.47
1.67
11.7
70.5
85.5
Phosphoric acid
H3PO4
97.10
1.70
14.8
85.5
67.5
Pyridine
C5H5N
79.10
0.982
12.4
100
80.6
Sulfuric acid
H2SO4
98.08
1.84
18.0
96
55.8
Triethanolamine
C6H15NO3
149.19
1.124
7.53
100
132.7
* V (mL) = volume in milliliters needed to prepare 1 L of 1 molar solution (1 M)
Approximate pH for different concentrations of various substances

Reagent
1 N
0.1 N
0.01 N
0.001 N
Acetic acid (glacial)
2.4
2.9
3.4
3.9
Ammonia
11.8
11.3
10.8
10.3
Benzoic acid
3.1
Citric acid
2.1
2.6
Hydrochloric acid
0.10
1.07
2.02
3.01
Hydrogen cyanide
5.1
Potassium hydroxide
14.0
13.0
12.0
11.0
Sodium bicarbonate
8.4
Sodium carbonate
11.5
11.0
Sodium hydroxide
14.05
13.07
12.12
11.13
Sulfuric acid
0.3
1.2
2.1

Equivalences % / M / N and preparation
The following table lists equivalences between molarities, normalities and percent solutions along with volume of desired substance needed to make 1 L of molar solutions.
HCl
0.01 M
0.1 M
1 M
2 M
3 M
5 M
6 M
10 M
12.1 M
Normality
0.01 N
0.1 N
1 N
2 N
3 N
5 N
6 N
10 N
12.1 N
% equivalent
0.08%
0.8%
8%
17%
25%
41%
50%
83%
100%
V needed to make 1 L
0.83 mL
8.3 mL
83 mL
165 mL
248 mL
413 mL
496 mL
826 mL
1000 mL
H2SO4
0.01 M
0.1 M
1 M
2 M
3 M
5 M
6 M
9 M
10 M
12 M
15 M
18 M
Normality
0.02 N
0.2 N
2 N
4 N
6 N
10 N
12 N
18 N
20 N
24 N
30 N
36 N
% equivalent
0.06%
0.56%
5.6%
11%
17%
28%
33%
50%
56%
67%
83%
100%
V needed to make 1 L
0.56 mL
5.6 mL
56 mL
111 mL
167 mL
278 mL
333 mL
500 mL
556 mL
667 mL
833 mL
1000 mL
NaOH
0.01 M
0.1 M
1 M
2 M
5 M
10 M
15 M
20 M
25 M
27 M
Normality
0.01 N
0.1 N
1 N
2 N
5 N
10 N
15 N
20 N
25 N
27 N
weight needed to make 1 L
0.40 g
4.0 g
40 g
80 g
200 g
400 g
600 g
800 g
1000 g
1080 g
KOH
0.01 M
0.1 M
1 M
2 M
5 M
10 M
15 M
20 M
21 M
Normality
0.01 N
0.1 N
1 N
2 N
5 N
10 N
15 N
20 N
21 N
weight needed to make 1 L
0.56 g
5.61 g
56.1 g
112 g
280 g
561 g
841 g
1120 g
1178 g

Saturday, October 1, 2011

Rhodium(III)-Catalyzed Oxidative Coupling of 5-Aryl-1H-pyrazoles with Alkynes and Acrylates


Abstract

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[RhCp*Cl2]2-catalyzed oxidative coupling of 5-aryl-1H-pyrazoles with alkynes and acrylates has been achieved using Cu(OAc)2 as an oxidant. Coupling with alkynes afforded six-membered azacycles as a result of C–C and C–N coupling. Coupling with acrylates followed a process of diolefination and a subsequent aza-Michael cyclization.

Intermolecular Oxidative C–N Bond Formation under Metal-Free Conditions: Control of Chemoselectivity between Aryl sp2 and Benzylic sp3 C–H Bond




A new synthetic approach toward intermolecular oxidative C–N bond formation of arenes has been developed under transition-metal-free conditions. Complete control of chemoselectivity between aryl sp2 and benzylic sp3 C–H bond imidation was achieved by the choice of nitrogen sources, representatively being phthalimide and dibenzenesulfonimide, respectively.
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