97038-96-5

Usage

Uses

Used in Organic Synthesis:
1,3-dibromo-2-(2,6-dibromophenyl)benzene is used as a research intermediate for the preparation of triphenylenes, tetraphenylenes, and other related compounds. Its unique structure and reactivity make it a valuable building block in the synthesis of complex organic molecules, which can be further utilized in various applications across different industries.
Used in Chemical Research:
In the field of chemical research, 1,3-dibromo-2-(2,6-dibromophenyl)benzene is employed as a starting material for the development of new synthetic routes and methodologies. Its versatile reactivity allows researchers to explore novel reactions and transformations, leading to the discovery of new compounds with potential applications in various fields.
Used in Pharmaceutical Industry:
1,3-dibromo-2-(2,6-dibromophenyl)benzene may also find applications in the pharmaceutical industry as a precursor for the synthesis of bioactive compounds. Its unique structure can be modified and functionalized to create new molecules with potential therapeutic properties, contributing to the development of new drugs and treatments.
Used in Material Science:
In the field of material science, 1,3-dibromo-2-(2,6-dibromophenyl)benzene can be used as a building block for the development of new materials with specific properties. Its incorporation into polymers, for example, can lead to the creation of materials with improved thermal stability, electrical conductivity, or other desirable characteristics.

Synthetic route

1,3-dibromo-2-iodo-benzene (19821-80-8) → 2,2’,6,6’-tetrabromobiphenyl (97038-96-5)

Conditions	Yield
Stage #1: 1,3-dibromo-2-iodo-benzene With n-butyllithium; copper(ll) bromide In diethyl ether; hexane at -78℃; for 0.75h; Inert atmosphere; Schlenk technique; Stage #2: With nitrobenzene In diethyl ether; hexane at -78 - 20℃; for 6h;	60%
Stage #1: 1,3-dibromo-2-iodo-benzene With n-butyllithium In diethyl ether at -78℃; Ullman coupling; Stage #2: With nitrobenzene; copper(I) bromide Ullman coupling;	56%
Stage #1: 1,3-dibromo-2-iodo-benzene With n-butyllithium In diethyl ether; hexane at -78℃; for 1.08333h; Stage #2: With copper(ll) bromide In diethyl ether; hexane at -78℃; for 1.5h; chemoselective reaction;	48%

1,3-dibromobenzene (108-36-1) → 2,2’,6,6’-tetrabromobiphenyl (97038-96-5)

Conditions	Yield
Stage #1: 1,3-dibromobenzene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With copper(I) cyanide lithium chloride; p-benzoquinone In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	60%
Stage #1: 1,3-dibromobenzene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: With copper(l) cyanide; chloranil; lithium chloride	47%
Stage #1: 1,3-dibromobenzene With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With copper(l) cyanide; lithium chloride In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #3: With p-benzoquinone In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	42%
Multi-step reaction with 2 steps 1.1: n-butyllithium; lithium diisopropyl amide / hexane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 1.2: 20 °C 2.1: n-butyllithium; copper(ll) bromide / hexane; diethyl ether / 0.75 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 6 h / -78 - 20 °C View Scheme

4,6,2',6'-tetrabromo-biphenyl-2,4'-diyldiamine (854242-36-7) → 2,2’,6,6’-tetrabromobiphenyl (97038-96-5)

1,3-dibromo-2-iodo-benzene (19821-80-8) → 1,2,3-tribromobenzene (608-21-9) + 2,2’,6,6’-tetrabromobiphenyl (97038-96-5)

Conditions	Yield
With n-butyllithium; copper(ll) bromide 1.) ether, hexane, -78 deg C, 2 h, 2.) ether, hexane, from -78 deg C to RT, 12 h; Multistep reaction. Yields of byproduct given;

1,3-dibromo-2-iodo-benzene (19821-80-8) → 1,3-dibromo-2-chlorobenzene (19230-27-4) + 2,2’,6,6’-tetrabromobiphenyl (97038-96-5)

Conditions	Yield
With n-butyllithium; copper dichloride 1.) ether, hexane, -78 deg C, 2 h, 2.) ether, hexane, from -78 deg C to RT, 12 h; Multistep reaction. Yields of byproduct given;
With n-butyllithium; copper dichloride 1.) ether, hexane, -78 deg C, 2 h, 2.) ether, hexane, from -78 deg C to RT, 12 h; Yield given. Multistep reaction;

2,2',4,4',6,6'-hexabromo-1,1'-biphenyl (59261-08-4) → 2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + 2,4,2’,4’-tetrabromobiphenyl (66115-57-9) + 2,4,2',6'-tetrabromo-biphenyl (97038-95-4)

Conditions	Yield
Stage #1: 2,2',4,4',6,6'-hexabromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	A 6 %Chromat. B 30 %Chromat. C 63 %Chromat.

2,6-dibromoaniline (608-30-0) → 2,2’,6,6’-tetrabromobiphenyl (97038-96-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / 0.17 h / 0 °C 1.2: 3 h / 0 °C 1.3: 0.5 h / 0 °C 2.1: n-butyllithium / diethyl ether; hexane / 1.08 h / -78 °C 2.2: 1.5 h / -78 °C View Scheme

chloro-trimethyl-silane (75-77-4) + 2,2’,6,6’-tetrabromobiphenyl (97038-96-5) → trimethyl(2',6,6'-tribromo-1,1'-biphenyl-2-yl)silane (911297-83-1)

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran at -80℃; Stage #2: chloro-trimethyl-silane In tetrahydrofuran	100%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -75℃; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -75 - 25℃; Further stages.;	88%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + bis(pinacol)diborane (73183-34-3) → 4,4'-bis(pinacolatoboronyl)-2,2'6,6'-tetrabromobiphenyl (1356238-72-6)

Conditions	Yield
(1,5-cyclooctadiene)(methoxy)iridium(I) dimer In further solvent(s) tert-butylmethyl ether, 60°C;	93%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether for 21h; Inert atmosphere; Reflux;	91%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) → 2,2,,6-tribromobiphenyl (507241-82-9)

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes at -75℃; Stage #2: With methanol; water In tetrahydrofuran; hexanes	91%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes at -75℃; Stage #2: With methanol In tetrahydrofuran; hexanes Product distribution / selectivity;	91%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes Stage #2: With methanol Product distribution / selectivity;	91%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes Stage #2: With methanol In tetrahydrofuran; hexanes	91%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → (6,6'-dibromobiphenyl-2,2'-diyl)dicarbaldehyde (1141733-49-4, 1260376-09-7, 1260376-17-7)

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #3: With hydrogenchloride In water; ethyl acetate	90%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran Stage #2: N,N-dimethyl-formamide	85%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran Stage #2: N,N-dimethyl-formamide In tetrahydrofuran	72%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium; (1R,2R)-bis(dimethylamino)cyclohexane In toluene at -78℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In toluene at -78 - 20℃; Inert atmosphere;

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + 1,2-dibromomethane (74-95-3) → 4,4,8,8-Tetrabrom-4,8-dihydrodibenzopentalen (33213-26-2)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 65℃; for 18h;	87%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + dimethylsilicon dichloride (75-78-5) → 1,9-dibromo-5,5-dimethyldibenzosilole (1187984-45-7)

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium Stage #2: dimethylsilicon dichloride	85%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + methyl iodide (74-88-4) → 2,6,6'-tribromo-2'-methoxy-1,1'-biphenyl (871707-37-8)

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -75℃; Stage #2: With sodium hydroxide; fluorodimethoxyborane diethyl etherate; dihydrogen peroxide In tetrahydrofuran; hexane at -75 - 25℃; Stage #3: methyl iodide With potassium hydroxide In dimethyl sulfoxide for 1h; Further stages.;	82%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes at -75℃; Stage #2: With sodium hydroxide; fluorodimethoxyborane diethyl etherate; dihydrogen peroxide In tetrahydrofuran; hexanes; water at -75℃; Stage #3: methyl iodide With hydrogenchloride; potassium hydroxide more than 3 stages;	82%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) → 2,2’-dibromo-6,6’-diiodo-1,1’-biphenyl

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃;	82%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) → 2,6,6'-tribromo-1,1'-biphenyl-2-ol (911297-81-9)

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -75℃; Stage #2: With sodium hydroxide; fluorodimethoxyborane diethyl etherate; dihydrogen peroxide In tetrahydrofuran; hexane at -75 - 25℃; Further stages.;	81%
Multi-step reaction with 2 steps 1.1: n-BuLi / hexane; tetrahydrofuran / -75 °C 1.2: hexane; tetrahydrofuran 2.1: aq. NaOH; H2O2 / tetrahydrofuran View Scheme
With sodium hydroxide; n-butyllithium; dihydrogen peroxide; fluorodimethoxyborane-diethyl etherate In tetrahydrofuran; hexane; water at -75℃;

chloromethyl formate (30566-31-5) + 2,2’,6,6’-tetrabromobiphenyl (97038-96-5) → 4,5‐dibromo‐9H‐fluoren‐9‐one (69414-97-7)

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: chloromethyl formate In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere;	78%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + methyl chloroformate (79-22-1) → 4,5‐dibromo‐9H‐fluoren‐9‐one (69414-97-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at 20℃;	78%
With tert.-butyl lithium In tetrahydrofuran; hexane at 20℃;	78%
With n-butyllithium In tetrahydrofuran; hexane at 20℃;	78%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + C24H30NPSn2 + 1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane (30404-92-3) → C36H23NO2P2

Conditions	Yield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;	73%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + C24H32NPSn2 + 1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane (30404-92-3) → C36H25NO2P2

Conditions	Yield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;	73%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + C24H32NPSn2 + 1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane (30404-92-3) → C36H25NO2P2

Conditions	Yield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;	73%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + C36H37N2OPSn2 + 1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane (30404-92-3) → C48H30N2O3P2

Conditions	Yield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;	73%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + C24H30NPSn2 → C48H30N2O2P2

Conditions	Yield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;	73%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) → 1,8-di-bromobiphenylene (180404-96-0) + 1,8,9,16-Tetrabromotetraphenylene

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Metallation; Stage #2: With zinc dibromide In tetrahydrofuran; hexane at -50℃; for 2h; Transmetallation; Stage #3: With copper dichloride In tetrahydrofuran; hexane at -78 - 20℃; Elimination; Substitution;	A 72% B n/a
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: With zinc dibromide In tetrahydrofuran; hexane at -50℃; for 2h; Stage #3: With copper dichloride In tetrahydrofuran; hexane at -78 - 20℃;	A 72% B n/a
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Metallation; Stage #2: With copper dichloride In tetrahydrofuran; hexane at -78 - 20℃; Elimination; Substitution;	A 15% B 61%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: With copper dichloride In tetrahydrofuran; hexane at -78℃;	A 15% B 61%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + 10-((2-methoxyethoxy)methyl)-9(10H)-acridinone (147643-41-2) → 9,9'-(6,6'-dibromo-2,2'-biphenyldiyl)diacridine (1141733-47-2)

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 10-((2-methoxyethoxy)methyl)-9(10H)-acridinone In tetrahydrofuran; hexane at -78 - 23℃; Stage #3: With hydrogenchloride In ethanol; water at 23℃; for 3h;	71%

xanth-9-one (90-47-1) + 2,2’,6,6’-tetrabromobiphenyl (97038-96-5) → 6,6'-dibromo-2,2'-bis(9-hydroxyxanthen-9-yl)biphenyl (500719-34-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;	68%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + chloro-diphenylphosphine (1079-66-9) → C36H26Br2P2 + (M)-(6,6'-dibromo-[1,1'-biphenyl]-2,2'-diyl)bis(diphenylphosphine)

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium; (1R,2R)-1,2-diphenyl-1,2-dimethoxyethane In hexane; toluene at -78℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: chloro-diphenylphosphine In tetrahydrofuran; hexane; toluene at -78 - 20℃; for 12h; Schlenk technique; Inert atmosphere; Overall yield = 80 %; Overall yield = 545 mg;	A n/a B 61%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + C24H30NPSn2 → C48H30N2O2P2

Conditions	Yield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;	60%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + C19H26NPSn2 → C38H22N2O2P2

Conditions	Yield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;	60%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → (S)-6,6'-dibromo[1,1'-biphenyl]-2,2'-dicarbaldehyde

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With (S,S)-1,2-di(3H-dinaphtho[2,1-c:1',2'-e]azepin-4(5H)-yl)ethane; sec.-butyllithium In hexane; cyclohexane; toluene at -78℃; for 1.5h; Inert atmosphere; Schlenk technique; Stage #2: N,N-dimethyl-formamide In hexane; cyclohexane; toluene at -78℃; Reagent/catalyst; Inert atmosphere; Schlenk technique; enantioselective reaction;	50%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + chlorodicyclohexylphosphane (16523-54-9) → C36H50Br2P2 + (M)-(6,6'-dibromo-[1,1'-biphenyl]-2,2'-diyl)bis(dicyclohexylphosphine)

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium; (1R,2R)-1,2-diphenyl-1,2-dimethoxyethane In hexane; toluene at -78℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane; toluene at -78 - 20℃; for 12h; Schlenk technique; Inert atmosphere; Overall yield = 92 %; Overall yield = 650 mg;	A n/a B 46%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + phenyllithium (591-51-5) → C18H11Br3 (1171115-57-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); zinc(II) chloride In tetrahydrofuran at -80 - 20℃; Negishi coupling reaction;	42%

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + 1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane (30404-92-3) → C24H16P2 (1356238-70-4) + trans/cis-4,8-diphenyl-4,8-dihydrophosphindolo [4,3,2-bcd]phosphindole 4,8-dioxide

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl; 1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane With 1,1'-azobis(1-cyanocyclohexanenitrile) In 4-methyl-1,2,3-trifluorobenzene at 125℃; for 45h; Inert atmosphere; Stage #2: With dihydrogen peroxide In dichloromethane; water; 4-methyl-1,2,3-trifluorobenzene at 20℃; for 1h; Inert atmosphere;	A 41% B n/a

2,2’,6,6’-tetrabromobiphenyl (97038-96-5) + phenyldiiodoarsine (6380-34-3) → 4,5-dibromo-9-phenyl-9-arsafluorene

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: phenyldiiodoarsine In tetrahydrofuran; hexane at 20℃; for 14h; Inert atmosphere;	40%

1,4-dibromo-butane (110-52-1) + 2,2’,6,6’-tetrabromobiphenyl (97038-96-5) → (M)-1,12-dibromo-5,6,7,8-tetrahydrodibenzo[a,c][8]annulene + C16H14Br2

Conditions	Yield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium; (1R,2R)-1,2-diphenyl-1,2-dimethoxyethane In hexane; toluene at -78℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: 1,4-dibromo-butane With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane; toluene at -78 - 20℃; for 72h; Schlenk technique; Inert atmosphere; Overall yield = 51 %; Overall yield = 395 mg;	A 27% B n/a

Upstream product

• 854242-36-7 4,6,2',6'-tetrabromo-biphenyl-2,4'-diyldiamine 
• 19821-80-8 1,3-dibromo-2-iodo-benzene 
• 108-36-1 1,3-dibromobenzene 
• 59261-08-4 2,2',4,4',6,6'-hexabromo-1,1'-biphenyl 
• 608-30-0 2,6-dibromoaniline 

Downstream Products

• 1356238-74-8 2'',3',5',6''-tetrabromo-1,1':4',1'':4'',1'''-quaterphenyl 
• 1356238-84-0 2'',3',5',6''-tetrabromo-N⁽⁴⁾,N⁽⁴⁾,N(4'''),N(4''')-tetraphenyl-[1,1':4',1'':4'',1'''-quaterphenyl]-4,4'''-diamine 
• 1356238-70-4 C₂₄H₁₆P₂ 
• 1356238-72-6 4,4'-bis(pinacolatoboronyl)-2,2'6,6'-tetrabromobiphenyl 
• 1400915-93-6 C₃₀H₂₂Si 

Relevant academic research and scientific papers

Asymmetric Bromine-Lithium Exchange: Application toward the Synthesis of New Biaryl-Diphosphine Ligands

The desymmetrization of the prochiral tetrabromobiphenyl via asymmetric bromine-lithium exchange as a key step of synthesis of novel biphenyl-diphosphine ligands is reported. This new approach allows an easy access to twelve new enantiomerically pure atropisomeric ligands in one- to three-step reactions in good to excellent yields.

Synthetic method for optically pure double-helix oligomeric tetra-benzocyclooctene substances

The invention discloses a synthetic method for optically pure double-helix oligomeric tetra-benzocyclooctene substances. The synthetic method comprises the following steps: (1) carrying out oxidative cross-coupling on diiodo dimethoxy biphenyl (51) and 2,2',6,6'-biphenyl tetrabromide (97) to obtain 1,16-dibromo-8,9-dimethoxy tetra-benzocyclooctene (96); (2) splitting the compound (96), thus obtaining optically pure (S, S)-96 and (R, R)-96; (3) taking the compound (96) as a raw material, synthesizing an intermediate (116) containing 6 benzene rings; (4) splitting the intermediate (116) to obtain (M)-116 and (P)-116; (5) making the optically pure (S, S)-96 and (M)-116 reacted to obtain target products, namely (M) -117, (M)-149 and (M)-150; and/or: making the (R, R)-96 and (P)-116 reacted to obtain target products, namely (P)-117, (P)-149 and (P)-150.

Synthesis and Physical Properties of Strained Doubly Phosphorus-Bridged Biaryls and Viologens

New P/N-containing π-electron systems comprising fully planar biaryl arrays are synthesized by multiple radical phosphanylation. The biaryl moiety in these highly strained planar π-systems is rigidified by double P-bridging. The electronic properties of the core biaryl entity are varied by introducing N-donor substituents or by installing N-atoms within the π-system, thereby moving to the viologen core structure. The electrochemical and photophysical properties of these compounds are discussed and compared with those of related systems.

Catalytic asymmetric bromine-lithium exchange: A new tool to build axial chirality

We present here the first catalytic desymmetrization of the 2,2′,6,6′-tetrabromobiphenyl 1 and analogues, by a bromine-lithium exchange catalyzed by either diamines or diether derivatives (0.5 equiv.), yielding axially chiral compounds in high yield (up to 89%) and high enantioselectivity (up to 82%).

Drastic change in racemization barrier upon redox reactions: Novel chiral-memory units based on dynamic redox systems

The helical configuration of dication dyes 22+ with a dihydrodibenzoxepin unit remained unchanged even at high temperature, whereas the corresponding neutral electron donors 1 with a tetrahydrophenanthroxepin skeleton easily underwent racemization. Due to their electrochemical bistability, electron exchange between 1 and 22+ is prohibited. Thus, the above electrochromic pairs can serve as novel chiral-memory units where redox reactions trigger switching between an "erasable/writable"-state (1) and a "memorizing"-state (22+).

PROCESS FOR THE SYNTHESIS OF 2,2',6-TRIBROMOBIPHENYL

A process for the synthesis of 2,2′,6-tribromobiphenyl.

Chiral bromine-lithium exchange catalyzed by diamines

Different classes of prochiral polyhalide compounds have been tested in a chiral bromine-lithium exchange in the presence of different diamines with enantiomeric excesses of up to 63%.

Process for the synthesis of 2,2 ,6-tribromobiphenyl

A process for the synthesis of 2,2',6-tribromobiphenyl

PROCESS FOR THE SYNTHESIS OF 2,2',6-TRIBROMOBIPHENYL

A process for the synthesis of 2,2',6-tribromobiphenyl.

PROCESS FOR THE PREPARATION OF ASYMMETRICALLY SUBSTITUTED BIARYLDIPHOSPHINES

Provided is a process for the preparation of asymmetrically substituted biaryldiphosphine ligands of the formula, (I) wherein R1 is C1-6-alkyl or C3-10-cycloalkyl optionally substituted with one or more halogen atoms, and R2 and R3 are equal and are C5-10-cycloalkyl or C1-6-alkyl, or R2 is C5-10-cycloalkyl or C1-6-alkyl, and R3 is aryl optionally substituted with one or more substituents selected from the group consisting of halogen atoms, nitro, amino, C1-6-alkyl, C1-6-alkoxy and di-C1-6-alkylamino groups, and each C1-6-alkyl, C1-6-alkoxy, di-C1-6-alkylamino and C5-10-cycloalkyl group in R2 and R3 optionally being substituted with one or more halogen atoms, from 2,2’, 6, 6’-tetra-bromobiphenyl by a sequence of bromine-metal exchanges and subsequent reactions.