An efficient and simple protocol for a PdCl2-ligandless and additive-free Suzuki coupling reaction of aryl bromides

doi:10.1016/j.tetlet.2011.09.115 

Expeditious synthesis of 3,4-dihydroisocoumarins and phthalides using the Heck–Matsuda reaction

doi:10.1016/j.tetlet.2011.09.014 

Pyridine synthesis from oximes and alkynes via rhodium(iii) catalysis: Cp* and Cpt provide complementary selectivity

Tomislav Rovis, Chem. Commun., 2011, 47, 11846-11848

Ruthenium-Catalyzed Isoquinolone Synthesis through C[BOND]H Activation Using an Oxidizing Directing Group

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

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

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

Organometallics, 2011, DOI: 10.1021/om200451v

NiCl2(PMe3)2-Catalyzed Borylation of Aryl Chlorides

2011, OL, DOI: 10.1021/ol202267t

Oxidative C–H Homodimerization of Phenylacetamides

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

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

2011, OL, DOI: 10.1021/ol202677g

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

OL, 2011, DOI: 10.1021/ol202552y

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

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

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

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

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

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

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

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

Innate and Guided C–H Functionalization Logic

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

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

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

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

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

C–H Bond Activation at Palladium(IV) Centers

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

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

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

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

Naohiko Yoshikai, JACS 2011, DOI: 10.1021/ja2047073

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

Eiichi Nakamura, JACS 2011, DOI: 10.1021/ja209300c

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

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

A Versatile Synthesis of Substituted Isoquinolines

doi/10.1002/anie.201104769

Copper-Catalyzed Oxidative CO Coupling by Direct CH Bond Activation of Formamides: Synthesis of Enol Carbamates and 2-Carbonyl-Substituted Phenol Carbamates

Use of Hemilabile N,N Ligands in Nitrogen-Directed Iridium-Catalyzed Borylations of Arenes

DOI: 10.1002/anie.201104544

Amination of Benzoxazoles and 1,3,4-Oxadiazoles Using 2,2,6,6-Tetramethylpiperidine-N-oxoammonium Tetrafluoroborate as an Organic Oxidant

DOI: 10.1002/anie.201104735

Rhodium-Catalyzed Annulation of N-Benzoylsulfonamide with Isocyanide through C[BOND]H Activation

DOI: 10.1002/chem.201102475

A Diruthenium Catalyst for Selective, Intramolecular Allylic C–H Amination

A Diruthenium Catalyst for Selective, Intramolecular Allylic C–H Amination: Reaction Development and Mechanistic Insight Gained through Experiment and Theory

JACS, 2011, DOI: 10.1021/ja203576p

Copper-Mediated C–H Activation/C–S Cross-Coupling of Heterocycles with Thiols - The Journal of Organic Chemistry (ACS Publications)

JOC 2011, DOI: 10.1021/jo2017444

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

Abstract

[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.