Synthetic Circuit 1
Reference
Monoalkylation of dichloroarenes with Grignard reagents catalyzed by a nickel complex
Reddy, G. S.;
Tam, Wilson,
Organometallics,
1984,
3(4),
630-2
Synthetic Circuit 2
1.1
Catalysts:
Palladium diacetate
Solvents:
Acetonitrile
Reference
The Stille reaction
Farina, Vittorio;
Krishnamurthy, Venkat;
Scott, William J.,
Organic Reactions (Hoboken,
1997,
50,
Synthetic Circuit 3
Reference
Electroreduction of organic compounds. 19. Formation of benzoanellated sulfur heterocycles by intramolecular cathodic cyclization of dithiocarboxylic esters
Gade, Thomas;
Streek, Michael;
Voss, Juergen,
Chemische Berichte,
1992,
125(1),
127-41
Synthetic Circuit 4
1.1
Reagents:
Potassium chloride
Catalysts:
Benzyltriethylammonium chloride
,
N,N,N′,N′-Tetramethylethylenediamine
,
Cupric chloride
,
Cuprous chloride
Solvents:
Acetonitrile
;
30 min
1.2
Solvents:
Acetonitrile
;
20 °C; 1 h, 20 °C
Reference
Cu(I)/Cu(II)/TMEDA, new effective available catalyst of Sandmeyer reaction
Sigeev, A. S.;
Beletskaya, I. P.;
Petrovskii, P. V.;
Peregudov, A. S.,
Russian Journal of Organic Chemistry,
2012,
48(8),
1055-1058
Synthetic Circuit 5
1.1
Reagents:
2-Nitrotoluene
,
Chlorine
Catalysts:
Antimony pentachloride
Reference
Preparation of chloro aromatic compounds
,
Japan,
,
,
Synthetic Circuit 6
1.1
Reagents:
1,3-Dichloro-5,5-dimethylhydantoin
Catalysts:
Sodium methoxide
Solvents:
Methanol
,
Acetonitrile
;
rt; rt → 60 °C; 8 - 16 h, 60 °C; 60 °C → rt
1.2
Reagents:
Sodium sulfite
Solvents:
Water
;
rt
Reference
Facile synthesis of 2-bromo-3-fluorobenzonitrile: An application and study of the halodeboronation of arylboronic acids
Szumigala, Ronald H. Jr.;
Devine, Paul N.;
Gauthier, Donald R. Jr.;
Volante, R. P.,
Journal of Organic Chemistry,
2004,
69(2),
566-569
Synthetic Circuit 7
1.1
Reagents:
Isoamyl nitrite
Solvents:
Acetone
;
0 °C; 0 - 15 °C
1.2
Reagents:
Cuprous chloride
Solvents:
Ethanol
;
< 5 °C; 20 min, < 5 °C; rt; 2 h, rt
Reference
Method for preparing aryl diazonium chlorocuprate
,
China,
,
,
Synthetic Circuit 8
Reference
Radiohalogenation of nonactivated aromatic compounds via aryltrimethylsilyl intermediates
Wilbur, D. S.;
Anderson, K. W.;
Stone, W. E.;
O'Brien, H. A. Jr.,
Journal of Labelled Compounds and Radiopharmaceuticals,
1982,
19(10),
1171-88
Synthetic Circuit 9
Reference
Allyl chloride-induced radical chlorination of alkylaromatic compounds
Serguchev, Yu. A.;
Barabash, V. B.;
Stetsyuk, G. A.,
Ukrainskii Khimicheskii Zhurnal (Russian Edition),
1989,
55(2),
198-201
Synthetic Circuit 10
1.1
Reagents:
Hydrogen sulfide
Reference
High-temperature organic synthesis. XXII. Thermal transformations of exo-chloro-substituted derivatives of toluene
Voronkov, M. G.;
Deryagina, E. N.;
Shagun, L. G.;
Vitkovskii, V. Yu.,
Zhurnal Organicheskoi Khimii,
1983,
19(5),
1079-84
Synthetic Circuit 11
1.1
Reagents:
Chlorosuccinimide
Catalysts:
1-(1,1-Dimethylethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate
(MCM-41 supported copper chloride complex)
Solvents:
Acetonitrile
;
12 h, 80 °C
Reference
A highly efficient heterogeneous copper-catalyzed chlorodeboronation of arylboronic acids leading to chlorinated arenes
He, Wen;
Zhang, Rongli;
Cai, Mingzhong,
RSC Advances,
2017,
7(2),
764-770
Synthetic Circuit 12
1.1
Catalysts:
Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]dirhodium
,
(Diphenylphosphino)ferrocene
Solvents:
Tetramethylurea
Reference
Novel Rh(I)-catalyzed reaction of arylzinc compounds with methyl halides
Hossain, Kabir M.;
Takagi, Kentaro,
Chemistry Letters,
1999,
(11),
1241-1242
Synthetic Circuit 13
1.1
Reagents:
Potassium chloride
,
Potassium bisulfate
Catalysts:
Chromate(1-), chlorotrioxo-, (T-4)-, hydrogen, compd. with isoquinoline (1:1:1)
Solvents:
1,2-Dichloroethane
;
30 - 40 min, rt
Reference
Rate enhancements due to ultrasound in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic compounds in presence of KHSO4/KCl
Rajanna, K. C.;
Rao, A. Sambashiva;
Chakravarthi, I. E.;
Reddy, K. Rajendar,
Asian Journal of Chemistry,
2018,
30(1),
167-170
Synthetic Circuit 14
1.1
Reagents:
Cuprous chloride
(alumina-supported)
Solvents:
tert-Butylbenzene
Reference
Halogen exchange reactions of aryl halides using supported copper(I)
Clark, James H.;
Jones, Craig W.;
Duke, Catherine V. A.;
Miller, Jack M.,
Journal of Chemical Research,
1989,
(8),
Synthetic Circuit 15
1.1
Reagents:
Chlorosuccinimide
Catalysts:
Cuprous chloride
Solvents:
Acetonitrile
;
2 h, 80 °C
Reference
Copper-Catalyzed Chlorination of Functionalized Arylboronic Acids
Wu, Hong;
Hynes, John,
Organic Letters,
2010,
12(6),
1192-1195
Synthetic Circuit 16
1.1
Reagents:
1-Propanethiol
,
Sodium hydroxide
Solvents:
N-Methyl-2-pyrrolidone
Reference
Preparation of thiophenols from unactivated aryl chlorides and sodium alkanethiolates in N-methyl-2-pyrrolidone
Shaw, James E.,
Journal of Organic Chemistry,
1991,
56(11),
3728-9
Synthetic Circuit 17
1.1
Reagents:
Isoamyl nitrite
Solvents:
Dimethylformamide
1.2
Reagents:
Cupric chloride
Solvents:
Dimethylformamide
;
338 K
Reference
Continuous-Flow Generation of Anhydrous Diazonium Species: Monolithic Microfluidic Reactors for the Chemistry of Unstable Intermediates
Fortt, Robin;
Wootton, Robert C. R.;
de Mello, Andrew J.,
Organic Process Research & Development,
2003,
7(5),
762-768