5345-47-1

Basic information

• Product Name: 2-Aminonicotinic acid
• Synonyms: NSC 3049;2-AMino-3-carboxypyridine;Nicotinic acid, 2-aMino- (6CI,7CI,8CI);2-Aminopyridine-3-carboxylic acid, 2-Amino-3-carboxypyridine;2- aMinoacid;2-Aminopyridin-3-carboxylic acid for synthesis;2-AMINO-3-PYRIDINECARBOXYLIC ACID;2-AMINOPYRIDINE-3-CARBOXYLIC ACID
• CAS NO: 5345-47-1
• Molecular Formula: C6H6N2O2
• Molecular Weight: 138.12
• EINECS: 226-296-3
• Product Categories: Building Blocks;C6;Chemical Synthesis;Heterocyclic Building Blocks;AMINOACID;Amines;blocks;Carboxes;Pyridines;Amino Acids and Derivatives;Heterocycles;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Pyridine;Pyridines derivates;Carboxylic Acids;Aromatics
• Mol File: 5345-47-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 295-297 °C (dec.)(lit.)
• Boiling Point: 253.51°C (rough estimate)
• Flash Point: 160.824 °C
• Appearance: Off-white to light yellow/Crystalline Powder
• Density: 1.3471 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO
• PKA: 2.94±0.10(Predicted)
• Water Solubility: soluble
• BRN: 119031
• CAS DataBase Reference: 2-Aminonicotinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminonicotinic acid(5345-47-1)
• EPA Substance Registry System: 2-Aminonicotinic acid(5345-47-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 5345-47-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to light yellow crystalline powder

Uses

Different sources of media describe the Uses of 5345-47-1 differently. You can refer to the following data:
1. A component of hair dyes.
2. 2-Aminopyridine-3-carboxylic acid can be used as:A ligand to prepare copper(II)-organic coordination compounds.A reactant to prepare pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolines by reacting with trimethylsilyl cyanide and phthalaldehyde.A reactant to synthesize organo-soluble and thermally stable poly(thiourea-amide-imide) polymers.

Definition

ChEBI: An aminonicotinic acid in which the amino group is situated at position 2 of the pyridine ring.

InChI:InChI=1/C6H6N2O2/c7-5-4(6(9)10)2-1-3-8-5/h1-3H,(H2,7,8)(H,9,10)

Synthetic route

2-Aminocarbonylnicotinic acid → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
With bromine; sodium hydroxide at 5 - 85℃; for 2.5h;	98.2%

2-hydroxycarbamoyl-nicotinic acid (23411-03-2) → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
In formamide at 130 - 150℃; for 20h;	83.5%

Pyridine-2,3-dicarboxylic acid bis-hydroxyamide (88423-10-3) → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
In formamide at 130 - 150℃; for 20h;	80%

2-chloronicotinic acid (2942-59-8) → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate In 1-methyl-pyrrolidin-2-one at 110℃; for 12h;	72%

2-chloronicotinic acid (2942-59-8) → 2-hydroxy-3-carboxypyridine (609-71-2) + 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
With ammonium hydroxide at 155℃; for 20h;	A n/a B 60%

2-amino-3-pyridinecarbonitrile (24517-64-4) → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
With hydrogenchloride at 175℃;

N-(2-pyridyl-3-methyl)acetamide (7463-30-1) → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
With potassium permanganate Erwaermen des Reaktionsprodukts mit wss. HCl;

2-benzenesulfonylamino-nicotinic acid (861045-11-6) → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
With hydrogenchloride at 175℃;

sulfuric acid (7664-93-9) + 3-hydroxy-1-nitroso-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid → 2-aminopyridin-3-carboxylic acid (5345-47-1)

6H-12H-dipyrido[2,3-b:2',3'-f][1,5]diazocine-5,11-dione (1000681-77-5) + acids → 2-aminopyridin-3-carboxylic acid (5345-47-1)

2-Aminocarbonylnicotinic acid (5860-70-8) + alkaline sodium hypobromite solution → 2-aminopyridin-3-carboxylic acid (5345-47-1)

6H-12H-dipyrido[2,3-b:2',3'-f][1,5]diazocine-5,11-dione (1000681-77-5) + alkaline solutions → 2-aminopyridin-3-carboxylic acid (5345-47-1)

2-methyl-1,2,3,4-tetrahydro-1,8-naphthyridine (861046-07-3) + aqueous KMnO4 → 2-aminopyridin-3-carboxylic acid (5345-47-1)

quinolinic acid α-amide → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
With sodium hypobromide

quinolinic acid imide → 2-aminopyridin-3-carboxylic acid (5345-47-1) + 3-amino-pyridine-carboxylic acid-(2)

Conditions	Yield
With alkaline sodium hypochlorite solution at 80℃;

2-[3,5-bis(trifluoromethyl)phenylsulfonyl]ethyl 2-aminonicotinate (548740-14-3) → 2-aminopyridin-3-carboxylic acid (5345-47-1) + 3,5-bis(trifluoromethyl)phenyl vinyl sulfone (548740-06-3)

Conditions	Yield
With sodium hydrogencarbonate In acetone at 20℃; for 12h;

nicotinic acid (59-67-6) + phenyl-β-pyridyl ketone → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / 30percent H2O2 / acetic acid / 3 h / 90 °C 2: PCl5, POCl3 3: 60 percent / conc. NH4OH / 20 h / 155 °C View Scheme
Multi-step reaction with 3 steps 1: 80 percent / 30percent H2O2 / acetic acid / 3 h / 90 °C 2: 65 percent / POCl3, Et3N / 4 h / 100 °C 3: 60 percent / conc. NH4OH / 20 h / 155 °C View Scheme

Nicotinic acid N-oxide (2398-81-4) → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl5, POCl3 2: 60 percent / conc. NH4OH / 20 h / 155 °C View Scheme
Multi-step reaction with 2 steps 1: 65 percent / POCl3, Et3N / 4 h / 100 °C 2: 60 percent / conc. NH4OH / 20 h / 155 °C View Scheme

2-chloro-3-pyridinecarbonitrile (6602-54-6) → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH3; ethanol / 177 °C 2: concentrated aqueous HCl / 175 °C View Scheme

nicotinamide N-oxide (1986-81-8) → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: PCl5; POCl3 / 115 - 120 °C 2: NH3; ethanol / 177 °C 3: concentrated aqueous HCl / 175 °C View Scheme

nicotinamide (98-92-0) → 2-aminopyridin-3-carboxylic acid (5345-47-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: aqueous H2O2; acetic acid 2: PCl5; POCl3 / 115 - 120 °C 3: NH3; ethanol / 177 °C 4: concentrated aqueous HCl / 175 °C View Scheme

2-aminopyridin-3-carboxylic acid (5345-47-1) + ethanol (64-17-5) → 2-aminopyridine-3-carboxylic acid ethyl ester (13362-26-0)

Conditions	Yield
Stage #1: 2-aminopyridin-3-carboxylic acid; ethanol With sulfuric acid for 16h; Heating / reflux; Stage #2: With sodium hydroxide In water pH=8;	100%
With sulfuric acid at 90℃; for 12h;	98.08%
With sulfuric acid at 90℃; for 12h;	98.08%

2-aminopyridin-3-carboxylic acid (5345-47-1) → 2-amino-3,4,5,6-tetrahydropyridine-3-carboxylic acid hydrochloride

Conditions	Yield
With hydrogenchloride; hydrogen; platinum(IV) oxide In ethanol under 1499.7 Torr; for 2h; Ambient temperature;	100%
With hydrogenchloride; PtO2 In methanol	1.22 g (100%)

2-aminopyridin-3-carboxylic acid (5345-47-1) + trimethyl orthoformate (149-73-5) → 3H-pyrido[2,3-d]pyrimidin-4-one (24410-19-3)

Conditions	Yield
With ammonia In methanol at 105℃; for 8h;	100%

2-aminopyridin-3-carboxylic acid (5345-47-1) + diethyl cyanophosphonate (2942-58-7) + 4-methoxy-benzylamine (2393-23-9) → N-(4-methoxyphenyl)methyl-2-aminonicotinic acid amide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide	100%

potassium cyanate (590-28-3) + 2-aminopyridin-3-carboxylic acid (5345-47-1) → 1H-Pyrido[2,3-d]pyrimidine-2,4-dione (21038-66-4)

Conditions	Yield
With water; ammonium chloride at 80 - 200℃; for 2.5h;	99%
In water for 0.00833333h; microwave irradiation;	95%
With acetic acid In polyethyleneglycol (PEG-400) at 20 - 60℃; for 0.166667h;	78%
With ammonium chloride In water at 20 - 200℃; for 2.66667h;

2-aminopyridin-3-carboxylic acid (5345-47-1) → 2-amino-5-bromonicotinicacid (52833-94-0)

Conditions	Yield
With bromine In acetic acid	99%
With bromine In acetic acid	99%
With bromine In acetic acid at 20℃; for 20h;	98%

2-aminopyridin-3-carboxylic acid (5345-47-1) + H-Phe-OEt (3081-24-1) → (S)-ethyl 2-(2-aminonicotinamido)-3-phenylpropanoate (1003023-68-4)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide	98%

2-aminopyridin-3-carboxylic acid (5345-47-1) + methylamine hydrochloride (593-51-1) → 2-amino-N-methyl-nicotinamide (870997-87-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	98%

2-aminopyridin-3-carboxylic acid (5345-47-1) + tert-butylisonitrile (119072-55-8, 7188-38-7) + 3-nitro-benzaldehyde (99-61-6) → 3-(tert-butylamino)-2-(3-nitrophenyl)imidazo[1,2-a]pyridine-8-carboxylic acid (1608494-18-3)

Conditions	Yield
In ethanol at 50℃; for 3h;	98%

2-aminopyridin-3-carboxylic acid (5345-47-1) + 3-(trifluoromethyl)benzene-1-carbohydrazide (22227-25-4) → 2-amino-N′-(3-(trifluoromethyl)benzoyl)nicotinohydrazide

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃;	98%

2-aminopyridin-3-carboxylic acid (5345-47-1) + urea (57-13-6) → 2,4-dihydroxy-pyrido[2,3-d]pyrimidine (21038-66-4)

Conditions	Yield
at 280℃;	97%
at 195℃; for 1.5h;	76%
at 210℃; for 0.25h;	63.3%

2-aminopyridin-3-carboxylic acid (5345-47-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + Propargylamine (2450-71-7) → 3-(prop-2-ynyl)pyrido[2,3-d]pyrimidin-4(3H)-one (1064689-94-6)

Conditions	Yield
Stage #1: 2-aminopyridin-3-carboxylic acid; N,N-dimethyl-formamide dimethyl acetal In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 0.25h; Microwave irradiation; Inert atmosphere; Green chemistry; Stage #2: Propargylamine With acetic acid at 100℃; under 760.051 Torr; for 0.25h; Inert atmosphere; Microwave irradiation; Green chemistry;	97%

2-aminopyridin-3-carboxylic acid (5345-47-1) + Cyclohexyl isocyanide (931-53-3) + 4-methyl-benzaldehyde (104-87-0) → 3-(cyclohexylamino)-2-(4-methylphenyl)imidazo[1,2-a]pyridine-8-carboxylic acid (1608494-14-9)

Conditions	Yield
In ethanol at 50℃; for 3h;	97%

2-aminopyridin-3-carboxylic acid (5345-47-1) + orthoformic acid triethyl ester (122-51-0) → 2-(1H-tetrazol-1-yl)nicotinic acid

Conditions	Yield
With sodium azide In neat (no solvent) at 90℃; for 0.833333h; Reagent/catalyst; Green chemistry;	97%

2-aminopyridin-3-carboxylic acid (5345-47-1) + acetic anhydride (108-24-7) → 2-Methyl-4H-pyrido<2,3-d><3,1>oxazin-4-one (3809-93-6)

Conditions	Yield
at 170℃; for 1h;	96%
at 165 - 170℃; for 1h;	90%
for 2h; Inert atmosphere; Reflux;	79%

2-aminopyridin-3-carboxylic acid (5345-47-1) → (2-amino-3-pyridinyl)methanol (23612-57-9)

Conditions	Yield
Stage #1: 2-aminopyridin-3-carboxylic acid With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Heating / reflux; Stage #2: With sodium hydroxide In tetrahydrofuran; water for 0.25h;	96%
With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Heating;	96%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 18h; Reflux;	96%

2-aminopyridin-3-carboxylic acid (5345-47-1) + urea (57-13-6) → 1H-Pyrido[2,3-d]pyrimidine-2,4-dione (21038-66-4)

Conditions	Yield
In water for 0.075h; microwave irradiation;	95%
Stage #1: 2-aminopyridin-3-carboxylic acid; urea at 180 - 210℃; for 1.5h; Stage #2: With sodium hydroxide In water at 50℃;	82%
Stage #1: 2-aminopyridin-3-carboxylic acid; urea at 180 - 210℃; for 0.25h; Stage #2: With sodium hydroxide In water at 20 - 55℃;	76%

2-aminopyridin-3-carboxylic acid (5345-47-1) → 2-aminopyridine-3-carboxamide (13438-65-8)

Conditions	Yield
With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;	95%
With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;	89%
Stage #1: 2-aminopyridin-3-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran for 12h; Inert atmosphere; Stage #2: With ammonia In tetrahydrofuran Inert atmosphere;	77.7%

2-aminopyridin-3-carboxylic acid (5345-47-1) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 2-aminonicotinate (14667-47-1)

Conditions	Yield
In methanol; toluene at 0℃; for 0.5h;	95%
In methanol; diethyl ether; toluene at 0℃; for 0.75h; Inert atmosphere;	90%
In methanol; hexane for 0.5h;

2-aminopyridin-3-carboxylic acid (5345-47-1) → 2-aminopyridine-3-carboxylic acid ethyl ester (13362-26-0)

Conditions	Yield
With sulfuric acid In ethanol for 16h; Reflux;	95%

2-aminopyridin-3-carboxylic acid (5345-47-1) + tert-butylisonitrile (119072-55-8, 7188-38-7) + 2-nitro-benzaldehyde (552-89-6) → 3-(tert-butylamino)-2-(2-nitrophenyl)imidazo[1,2-a]pyridine-8-carboxylic acid (1608494-20-7)

Conditions	Yield
In ethanol at 50℃; for 3h;	95%

2-aminopyridin-3-carboxylic acid (5345-47-1) + Cyclohexyl isocyanide (931-53-3) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 3-(cyclohexylamino)-2-(2,4-dimethoxyphenyl)imidazo[1,2-a]pyridine-8-carboxylic acid

Conditions	Yield
In ethanol at 60℃; for 6h;	95%

2-aminopyridin-3-carboxylic acid (5345-47-1) + α-bromoacetophenone (70-11-1) → benzoylmethyl 2-amino-pyridine-3-carboxylate

Conditions	Yield
Stage #1: 2-aminopyridin-3-carboxylic acid With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 2h; Stage #2: α-bromoacetophenone In N,N-dimethyl-formamide at 50℃; for 3h;	94%

2-aminopyridin-3-carboxylic acid (5345-47-1) + 2-chloro-1,3-dimethyl imidazolium chloride → methyl 2-aminonicotinate (14667-47-1)

Conditions	Yield
With triethylamine In methanol at 20℃; for 1h;	94%

2-aminopyridin-3-carboxylic acid (5345-47-1) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(2-aminonicotinoyl)piperazine-1-carboxylate

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 60℃; for 2h; Inert atmosphere;	93.4%

methanol (67-56-1) + 2-aminopyridin-3-carboxylic acid (5345-47-1) → methyl 2-aminonicotinate (14667-47-1)

Conditions	Yield
With sulfuric acid at 0 - 60℃; under 760.051 Torr; for 1.5h; Inert atmosphere; Microwave irradiation;	93%
With thionyl chloride at 0 - 80℃; for 3h;	86%
With sulfuric acid at 80℃; for 7h;	63%

2-aminopyridin-3-carboxylic acid (5345-47-1) → 2-amino-5-bromonicotinic acid hydrobromide (52963-33-4)

Conditions	Yield
With bromine In acetic acid at 0 - 20℃; for 48h;	93%
With bromine; acetic acid at 20℃; for 1h;	93%
With bromine; acetic acid at 20℃; Cooling with ice;	91%

2-aminopyridin-3-carboxylic acid (5345-47-1) + Cyclohexyl isocyanide (931-53-3) + 3-nitro-benzaldehyde (99-61-6) → 3-(cyclohexylamino)-2-(3-nitrophenyl)imidazo[1,2-a]pyridine-8-carboxylic acid (1608494-16-1)

Conditions	Yield
In ethanol at 50℃; for 3h;	93%

2-aminopyridin-3-carboxylic acid (5345-47-1) + 2-chloro-3-(4-chlorophenyl)-1,8-naphthyridine (439277-55-1) → C20H11ClN4O (1075254-10-2)

Conditions	Yield
With acetic acid for 0.075h; microwave irradiation;	92%

Upstream product

• 7463-30-1 N-(2-pyridyl-3-methyl)acetamide 
• 5860-70-8 2-Aminocarbonylnicotinic acid 
• 1603-40-3 3-methylpyridin-2-ylamine 
• 23612-57-9 (2-amino-3-pyridinyl)methanol 
• 2942-59-8 2-chloronicotinic acid 
• 98-92-0 nicotinamide 
• 1986-81-8 nicotinamide N-oxide 
• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 2398-81-4 Nicotinic acid N-oxide 
• 59-67-6 nicotinic acid 
• 548740-14-3 2-[3,5-bis(trifluoromethyl)phenylsulfonyl]ethyl 2-aminonicotinate 
• 861046-07-3 2-methyl-1,2,3,4-tetrahydro-1,8-naphthyridine 
• 1000681-77-5 6H-12H-dipyrido[2,3-b:2',3'-f][1,5]diazocine-5,11-dione 
• 7664-93-9 sulfuric acid 

Downstream Products

• 28279-12-1 2-methylpyrido[2,3-d]pyrimidin-4(3H)-one 
• 14667-47-1 methyl 2-aminonicotinate 
• 16344-24-4 2-(phenylamino)nicotinic acid 
• 13362-26-0 2-aminopyridine-3-carboxylic acid ethyl ester 
• 37891-04-6 2-thioxo-2,3-dihydropyrido/2,3-d/pyrimidin-4(1H)-one 
• 1057318-86-1 2-(Carboxymethyl-amino)-nicotinsaeure 
• 21038-66-4 1H-Pyrido[2,3-d]pyrimidine-2,4-dione 
• 109104-21-4 2-[(N-acetyl-sulfanilyl)-amino]-nicotinic acid 
• 6760-14-1 2-amino-5-nitro-nicotinic acid 
• 393-55-5 2-fluoronicotinic acid 
• 17782-03-5 2-acetamidonicotinic acid 
• 74611-54-4 2-[((E)-But-2-enyl)amino]-nicotinic acid 
• 215734-32-0 2-Amino-N-(2,4-dimethoxy-benzyl)-nicotinamide 
• 34757-95-4 2-amino-N-isopropyl-nicotinamide 

Relevant articles and documents

Preparation method of 2-aminopyridine-3-carboxylic acid

The present invention discloses a method for preparing 2- aminopyridine-3-carboxylic acid, comprising the following steps: adding 500g of deionized water in a 1L three-mouth bottle, adding raw material 2-amino-3-methylpyridine 100g under stirring, adding a catalyst of 186g and heating to 55-65 ° C, and then controlling the temperature at 60-70 ° C in batches to add potassium permanganate 146g, after addition continue stirring reaction for 3 hours; then cooled to room temperature, filtered to remove black manganese dioxide and recovered After adjusting the PH to 2.5 in the aqueous phase, freezing to 3-7 ° C filtration, the white filter cake was obtained, and then washed and dried in ice water to give the product 2-amino 2-aminopyridine-3-carboxylic acid 65 grams. The preparation method of the intermediate 2-aminopyridine-3-carboxylic acid of this drug has reasonable design of the whole process, mild conditions, simple operation, easy raw materials and high generation efficiency. The reaction of this method is safe and controllable, and the obtained manganese dioxide by-products can be recycled, and the yield is high, which is conducive to industrial production.

Copper(ii)-catalyzed c-n coupling of aryl halides and n-nucleophiles promoted by quebrachitol or diethylene glycol

Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-Arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C-N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.

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