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1,3-Bis(diphenylphosphino)propane, also known as "dppp" or "tBuXPhos", is a bidentate phosphine ligand with a propane backbone and two diphenylphosphino groups attached to the 1,3-positions. It is a versatile and widely used ligand in coordination chemistry due to its steric and electronic properties, which can influence the reactivity and selectivity of various catalytic processes.

6737-42-4

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6737-42-4 Usage

Uses

Used in Coordination Chemistry:
1,3-Bis(diphenylphosphino)propane is used as a bidentate ligand for forming complexes with metal ions, such as the complex dichloro(1,3-bis(diphenylphosphino)propane)nickel, which is formed by reacting with nickel(II) chloride.
Used in Kumada Coupling Reaction:
1,3-Bis(diphenylphosphino)propane is used as a catalyst in the Kumada coupling reaction, a cross-coupling reaction between organohalides and Grignard reagents to form carbon-carbon bonds.
Used in Palladium-Catalyzed Reactions:
1,3-Bis(diphenylphosphino)propane acts as a ligand for palladium(II) catalysts, which are useful for the co-polymerization of carbon monoxide and ethylene to produce polyketones.
Used in Heck Reaction:
1,3-Bis(diphenylphosphino)propane is employed in palladium-catalyzed arylation under the Heck reaction, a method for forming carbon-carbon bonds between an alkene and an aryl halide.
Used in Suzuki Reaction:
1,3-Bis(diphenylphosphino)propane serves as a catalyst in the Suzuki reaction, a cross-coupling reaction between an organoboron compound and an organohalide to form carbon-carbon bonds.
Used in Negishi Coupling:
1,3-Bis(diphenylphosphino)propane is used as a catalyst in Negishi coupling reactions, a type of cross-coupling reaction involving organozinc reagents and various electrophiles.
Used in Sonogashira Coupling:
1,3-Bis(diphenylphosphino)propane is employed as a catalyst in Sonogashira coupling reactions, which involve the coupling of terminal alkynes with aryl or vinyl halides to form carbon-carbon bonds.

Check Digit Verification of cas no

The CAS Registry Mumber 6737-42-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,7,3 and 7 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 6737-42:
(6*6)+(5*7)+(4*3)+(3*7)+(2*4)+(1*2)=114
114 % 10 = 4
So 6737-42-4 is a valid CAS Registry Number.
InChI:InChI=1/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2

6737-42-4 Well-known Company Product Price

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  • TCI America

  • (B1138)  1,3-Bis(diphenylphosphino)propane  >98.0%(GC)

  • 6737-42-4

  • 5g

  • 230.00CNY

  • Detail
  • TCI America

  • (B1138)  1,3-Bis(diphenylphosphino)propane  >98.0%(GC)

  • 6737-42-4

  • 25g

  • 790.00CNY

  • Detail
  • Alfa Aesar

  • (A12931)  1,3-Bis(diphenylphosphino)propane, 97%   

  • 6737-42-4

  • 5g

  • 567.0CNY

  • Detail
  • Alfa Aesar

  • (A12931)  1,3-Bis(diphenylphosphino)propane, 97%   

  • 6737-42-4

  • 25g

  • 1919.0CNY

  • Detail
  • Alfa Aesar

  • (A12931)  1,3-Bis(diphenylphosphino)propane, 97%   

  • 6737-42-4

  • 100g

  • 6133.0CNY

  • Detail
  • Aldrich

  • (262048)  1,3-Bis(diphenylphosphino)propane  97%

  • 6737-42-4

  • 262048-1G

  • 250.38CNY

  • Detail
  • Aldrich

  • (262048)  1,3-Bis(diphenylphosphino)propane  97%

  • 6737-42-4

  • 262048-5G

  • 380.25CNY

  • Detail
  • Aldrich

  • (262048)  1,3-Bis(diphenylphosphino)propane  97%

  • 6737-42-4

  • 262048-25G

  • 1,279.98CNY

  • Detail

6737-42-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-Bis(diphenylphosphino)propane

1.2 Other means of identification

Product number -
Other names 3-diphenylphosphanylpropyl(diphenyl)phosphane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6737-42-4 SDS

6737-42-4Synthetic route

methanol
67-56-1

methanol

(propane-1,3-diyl)bis(diphenylphosphane)-borane(1:2)
100809-49-2

(propane-1,3-diyl)bis(diphenylphosphane)-borane(1:2)

A

Trimethyl borate
121-43-7

Trimethyl borate

B

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Conditions
ConditionsYield
In toluene at 100℃; Inert atmosphere;A n/a
B 98%
1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Conditions
ConditionsYield
Stage #1: chloro-diphenylphosphine With sodium In dibutyl ether at 105℃; for 2h;
Stage #2: 1.3-chlorobromopropane In dibutyl ether at 105℃; for 2h;
95%
(propane-1,3-diyl)bis(diphenylphosphane)-borane(1:2)
100809-49-2

(propane-1,3-diyl)bis(diphenylphosphane)-borane(1:2)

ethanol
64-17-5

ethanol

A

triethyl borate
150-46-9

triethyl borate

B

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Conditions
ConditionsYield
Inert atmosphere; Reflux;A n/a
B 94%
1,3-bis(diphenylphosphoryl)propane
16524-41-7

1,3-bis(diphenylphosphoryl)propane

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at 150℃; for 12h; Inert atmosphere;93%
With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate In various solvent(s) at 100℃; for 7h;91%
With diethoxymethylane; Bis(p-nitrophenyl) phosphate In toluene at 110℃; Inert atmosphere; chemoselective reaction;82%
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In toluene at 100℃; for 22h; Inert atmosphere; Sealed tube;80%
With hexylsilane; trifluorormethanesulfonic acid In toluene at 70℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;72 %Spectr.
1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

diphenylphosphane
829-85-6

diphenylphosphane

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Conditions
ConditionsYield
With cesium hydroxide; 4 Angstroem MS In N,N-dimethyl-formamide at 23℃; for 45h;83%
With cesium hydroxide; 4 A molecular sieve In N,N-dimethyl-formamide at 23℃; for 45h;83%
With tert-butylimino-tris(dimethylamino)phosphorane In tetrahydrofuran; diethyl ether for 24h; Ambient temperature;60%
C21H14N2O8
1273415-58-9

C21H14N2O8

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Conditions
ConditionsYield
With [Ir(ppy)2bpy]PF6; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 22℃; for 8h; Irradiation;82%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium triflate / tetrahydrofuran / 2.25 h / 0 °C / Inert atmosphere; Reflux
2: diisobutylaluminium hydride / toluene / 12 h / 150 °C / Inert atmosphere
View Scheme
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

diphenylphosphane
829-85-6

diphenylphosphane

A

diphenyl(3-bromopropyl)phosphine

diphenyl(3-bromopropyl)phosphine

B

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Conditions
ConditionsYield
Stage #1: n-butyllithium; diphenylphosphane In tetrahydrofuran; hexane at 20℃; for 0.833333h; Inert atmosphere;
Stage #2: 1,3-dibromo-propane In tetrahydrofuran; hexane at 20℃; for 0.333333h; Inert atmosphere; Overall yield = 396.6 mg;
latter phosphonate

latter phosphonate

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

dimethyl 1-octen-2-yl-phosphonate
174781-89-6

dimethyl 1-octen-2-yl-phosphonate

dimethyl (E)-octenylphosphonate

dimethyl (E)-octenylphosphonate

Conditions
ConditionsYield
In palladium diacetate100%
In 1,3-bis(dimethylphosphino)propane85%
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

A

tetracarbonyl-1,3-bis(diphenylphosphino)propane-molybdenum(0)
15553-68-1

tetracarbonyl-1,3-bis(diphenylphosphino)propane-molybdenum(0)

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
[Rh(dppp)(CO)2]2

[Rh(dppp)(CO)2]2

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

hydrogen
1333-74-0

hydrogen

RhH(CO)(C6H5)2PCH2CH2CH2P(C6H5)2(C6H5)2P(CH2)3P(C6H5)2
81524-37-0

RhH(CO)(C6H5)2PCH2CH2CH2P(C6H5)2(C6H5)2P(CH2)3P(C6H5)2

Conditions
ConditionsYield
In dichloromethane-d2 total pressure: 1 atm; 1.0-6.0 h; room temperature; dpp:Rh2 ratio=6.2:1;; no isolation; NMR-spectroscopic characterization;;100%
In dichloromethane-d2 total pressure: 1 atm; 10 h; room temperature; dpp:Rh2 ratio=19.8:1;; no isolation; NMR-spectroscopic characterization;;80%
In dichloromethane-d2 total pressure: 1 atm; 0.2 h; room temperature; dpp:Rh2 ratio=6.2:1; about 20-25 % unknown hydrides;; no isolation; NMR-spectroscopic characterization;;60%
With carbon monoxide In dichloromethane-d2 total pressure: 1 atm; 0.2 h; room temperature; dpp:Rh2 ratio=6.1:1;H2:CO=1:1; about 20-25 % unknown hydrides detected;; no isolation; NMR-spectroscopic characterization;;14%
chloromethyl(1,5-cyclooctadiene)palladium(II)

chloromethyl(1,5-cyclooctadiene)palladium(II)

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

[PdCl(CH3)(bis(diphenylphosphino)propane)]
139168-06-2

[PdCl(CH3)(bis(diphenylphosphino)propane)]

Conditions
ConditionsYield
In dichloromethane under N2 at room temp. in darkness, 1:1 mixt., stirred for 1.5 h; pptd., filtered, washed (ether), dried (vac.), NMR;100%
chlorobis(1,3-diphenylphosphinopropane)-exo-nido-[10-hydroorthocarborane-5,6,10-tris(hydrido)]ruthenium

chlorobis(1,3-diphenylphosphinopropane)-exo-nido-[10-hydroorthocarborane-5,6,10-tris(hydrido)]ruthenium

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

bis(1,3-diphenylphosphinopropane)chlororuthenium(II) nido-7,8-dicarbaundecaborate dichloromethane

bis(1,3-diphenylphosphinopropane)chlororuthenium(II) nido-7,8-dicarbaundecaborate dichloromethane

Conditions
ConditionsYield
In benzene benzene added to equimolar mixt. of Ru-carborane-complex and (PPh2)2(CH2)3, stirred at 22°C for 2-3 h; ppt. filtered off, washed (C6H6), recrystd. (CH2Cl2-hexane); elem. anal.;100%
chlorobis(1,3-diphenylphosphinopropane)-exo-nido-[7,8-dimethyl-10-hydroorthocarborane-5,6,10-tris(hydrido)]ruthenium(II) semidichloromethane

chlorobis(1,3-diphenylphosphinopropane)-exo-nido-[7,8-dimethyl-10-hydroorthocarborane-5,6,10-tris(hydrido)]ruthenium(II) semidichloromethane

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

bis(1,3-diphenylphosphinopropane)chlororuthenium(II) nido-7,8-dimethyl-7,8-dicarbaundecaborate dichloromethane

bis(1,3-diphenylphosphinopropane)chlororuthenium(II) nido-7,8-dimethyl-7,8-dicarbaundecaborate dichloromethane

Conditions
ConditionsYield
In benzene benzene added to equimolar mixt. of Ru-carborane-complex and (PPh2)2(CH2)3, stirred at 22°C for 2-3 h; ppt. filtered off, washed (C6H6), recrystd. (CH2Cl2-hexane); elem. anal.;100%
Pt(Sn(CH3)3)2(P(CH3C6H4)3)2

Pt(Sn(CH3)3)2(P(CH3C6H4)3)2

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Pt(Sn(CH3)3)2(C6H5)2P(CH2)3P(C6H5)2

Pt(Sn(CH3)3)2(C6H5)2P(CH2)3P(C6H5)2

Conditions
ConditionsYield
99%
dichloro(1,5-cyclooctadiene)palladium(II)
12107-56-1

dichloro(1,5-cyclooctadiene)palladium(II)

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

[1,3-bis(diphenylphosphino)propane]dichloridepalladium(II)
59831-02-6

[1,3-bis(diphenylphosphino)propane]dichloridepalladium(II)

Conditions
ConditionsYield
In dichloromethane for 2h; Inert atmosphere;99%
1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

N-(2-cyclopropylideneethyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide

N-(2-cyclopropylideneethyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide

cobalt(II) bromide

cobalt(II) bromide

C42H44CoNO2P2S

C42H44CoNO2P2S

Conditions
ConditionsYield
With zinc(II) iodide; zinc In acetonitrile at 20 - 25℃; for 2h; Inert atmosphere; Sealed tube;99%
2-trifluoromethanesulfonyloxy-8-acetylaminonaphthalene
168901-50-6

2-trifluoromethanesulfonyloxy-8-acetylaminonaphthalene

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

palladium diacetate
3375-31-3

palladium diacetate

8-acetylamino-2-naphthoic acid, methyl ester

8-acetylamino-2-naphthoic acid, methyl ester

Conditions
ConditionsYield
With dimethyl sulfoxide; triethylamine In methanol98.5%
hydrogenchloride
7647-01-0

hydrogenchloride

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

palladium
7440-05-3

palladium

bis(diphenylphosphino)propanepalladium(II) dichloride
59831-02-6

bis(diphenylphosphino)propanepalladium(II) dichloride

Conditions
ConditionsYield
Stage #1: hydrogenchloride; palladium With nitric acid In water
Stage #2: 1,3-bis-(diphenylphosphino)propane In water; N,N-dimethyl-formamide at 50℃; for 1h;
98.1%
di(pyridin-2-yl)amine
1202-34-2

di(pyridin-2-yl)amine

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

silver perchlorate

silver perchlorate

[Ag2(bis(2-pyridyl)amine)2(dppp)(ClO4)2]
936008-61-6

[Ag2(bis(2-pyridyl)amine)2(dppp)(ClO4)2]

Conditions
ConditionsYield
In acetonitrile stoich. mixt. in CH3CN stirred for 12 h at room temp.; evapd., washed (Et2O), elem. anal.;98%
2,2':6,2''-terpyridine
1148-79-4

2,2':6,2''-terpyridine

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

silver perchlorate

silver perchlorate

[Ag2(2,2':6',6''-terpyridyl)2(dppp)][ClO4]2

[Ag2(2,2':6',6''-terpyridyl)2(dppp)][ClO4]2

Conditions
ConditionsYield
In acetonitrile stoich. mixt. in CH3CN stirred for 12 h at room temp.; evapd., washed (Et2O), elem. anal.;98%
(C8H12)Pt(CH3C(O)NCH2COO)
142316-59-4

(C8H12)Pt(CH3C(O)NCH2COO)

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

((C6H5)2P(CH2)3P(C6H5)2)Pt(CH3C(O)NCH2COO)
142316-57-2

((C6H5)2P(CH2)3P(C6H5)2)Pt(CH3C(O)NCH2COO)

Conditions
ConditionsYield
In dichloromethane N2; stirred for 20 min at room temp.; evapd. to dryness under reduced pressure, crystd. from CH2Cl2/light petroleum; NMR;98%
(C8H12)Pt(CH3C(O)NCH(CH2C6H5)COO)

(C8H12)Pt(CH3C(O)NCH(CH2C6H5)COO)

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

((C6H5)2P(CH2)3P(C6H5)2)Pt(CH3C(O)NCH(CH2C6H5)COO)*H2O

((C6H5)2P(CH2)3P(C6H5)2)Pt(CH3C(O)NCH(CH2C6H5)COO)*H2O

Conditions
ConditionsYield
In dichloromethane N2; stirred for 15 min at room temp.; evapd. to dryness under reduced pressure, crystd. from CH2Cl2/light petroleum; NMR;98%
cis-dichloro(dimethylaminomethylene)(triphenylarsine)platinum(II)

cis-dichloro(dimethylaminomethylene)(triphenylarsine)platinum(II)

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

[1,3-bis(diphenylphosphino)propane](dimethylaminomethylene)(chloro)platinum(II) chloride - H2O (2/1)

[1,3-bis(diphenylphosphino)propane](dimethylaminomethylene)(chloro)platinum(II) chloride - H2O (2/1)

Conditions
ConditionsYield
With H2O In chloroform-d1 CDCl3; evapd., the residue was washed with pentane, crystd. from CH2Cl2-hexane (elem. anal.);98%
1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

Thiosalicylic acid
147-93-3

Thiosalicylic acid

[Ni(SC6H4CO2)(C27H26P2)]
195049-36-6

[Ni(SC6H4CO2)(C27H26P2)]

Conditions
ConditionsYield
With pyridine In methanol dissoln. of the Ni salt and the ligand in MeOH with warming, addn. of thiosalicylic acid, then pyridine, short reflux; filtration, washing (cold MeOH; Et2O), drying, recrystn. (CH2Cl2/Et2O); elem. anal.;98%
[(COD)Rh(μ-,kappa.O,O'-HCO2)]2
125979-15-9

[(COD)Rh(μ-,kappa.O,O'-HCO2)]2

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Rh(η(3)-cyclooctenyl)(Ph2P(CH2)3PPh2)
177283-23-7

Rh(η(3)-cyclooctenyl)(Ph2P(CH2)3PPh2)

Conditions
ConditionsYield
In tetrahydrofuran Ar-atmosphere; slow addn. of 1 equiv. of phosphine to Rh-complex soln. at -78°C, stirring for 20 min, slow warming to room temp., stirring for 30 min; solvent removal, drying (vac., 1 d);98%
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

dimercaptomaleonitrile disodium salt hydrate

dimercaptomaleonitrile disodium salt hydrate

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

(maleonitriledithilato)(1,3-bis(diphenylphosphino)propane)nickel(II)
635315-48-9

(maleonitriledithilato)(1,3-bis(diphenylphosphino)propane)nickel(II)

Conditions
ConditionsYield
In acetone mixt. of solids NiCl2*6H2O (1 mmol) and Ph2PCH2CH2CH2P(Ph)2 (0.41 g) in acetone stirred for 1 h; pptd. by H2O addn. with stirring; ppt. filtered off; washed (H2O, EtOH, Et2O); dried at room temp.; elem. anal.;98%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

{1,3-bis(diphenylphosphino)propane}platinumCl2
59329-00-9

{1,3-bis(diphenylphosphino)propane}platinumCl2

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 90℃; for 3h;98%

6737-42-4Relevant articles and documents

Catalytic Cleavage of Unactivated C(aryl)-P Bonds by Chromium

Ling, Liang,Luo, Meiming,Tang, Jinghua,Yuan, Shuqing,Zeng, Xiaoming

, p. 1581 - 1586 (2022/03/14)

We describe here the coupling to transform aryl phosphine derivatives by the cleavage of unactivated C(aryl)-P bonds with chromium catalysis, allowing us to achieve the reaction with alkyl bromides and arylmagnesium reagents under mild conditions. Mechani

Decarboxylative Phosphine Synthesis: Insights into the Catalytic, Autocatalytic, and Inhibitory Roles of Additives and Intermediates

Jin, Shengfei,Haug, Graham C.,Nguyen, Vu T.,Flores-Hansen, Carsten,Arman, Hadi D.,Larionov, Oleg V.

, p. 9764 - 9774 (2019/10/14)

Phosphines are among the most widely used ligands, catalysts, and reagents. Current synthetic approaches to phosphines are dominated by nucleophilic displacement reactions with organometallic reagents. Here, we report a radical-based approach to phosphines that proceeds by a cross-electrophile coupling of chlorophosphines and redox-active esters. The reaction allows for the synthesis of a broad range of substituted phosphines that were not readily attainable with the present methods. Our experimental and DFT computational studies also clarified the catalytic, autocatalytic, and inhibitory roles of additives and intermediates, as well as the mechanistic details of the photocatalytic and zinc-mediated redox modes that can have implications for the mechanistic interpretation of other cross-electrophile coupling reactions.

SPIROCYCLIC COMPOUNDS AS FARNESOID X RECEPTOR MODULATORS

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Paragraph 0667, (2019/05/15)

The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically acceptable salts or solvates thereof, wherein all the variables are as defined herein. These compounds modulate the activity of famesoid X receptor (FXR), for example, as agonists. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating a disease, disorder, or condition associated with FXR dysregulation, such as pathological fibrosis, transplant rejection, cancer, osteoporosis, and inflammatory disorders, by using the compounds and pharmaceutical compositions.

Highly Efficient and Robust Photocatalytic Systems for CO2 Reduction Consisting of a Cu(I) Photosensitizer and Mn(I) Catalysts

Takeda, Hiroyuki,Kamiyama, Hiroko,Okamoto, Kouhei,Irimajiri, Mina,Mizutani, Toshihide,Koike, Kazuhide,Sekine, Akiko,Ishitani, Osamu

, p. 17241 - 17254 (2019/01/04)

The development of highly efficient, selective, and durable photocatalytic CO2 reduction systems that only use earth-abundant elements is key for both solving global warming and tackling the shortage of energy and carbon resources. Here, we successfully developed CO2 reduction photocatalysts using [Cu2(P2bph)2]2+ (CuPS) (P2bph = 4,7-diphenyl-2,9-di(diphenylphosphinotetramethylene)-1,10-phenanthroline) as a redox photosensitizer and fac-Mn(X2bpy)(CO)3Br (Mn(4X)) (X2bpy = 4,4′-X2-2,2′-bipyridine (X = -H and -OMe) or Mn(6mes) (6mes = 6,6′-(mesityl)2-2,2′-bipyridne)) as the catalyst. The most efficient photocatalysis was achieved by Mn(4OMe): The total quantum yield of CO2 reduction products was 57%, the turnover number based on the Mn catalyst was over 1300, and the selectivity of CO2 reduction was 95%. Electronic and steric effects of the substituents (X) in the Mn complexes largely affected both the photocatalytic efficiency and the product selectivity. For example, the highest selectivity of CO formation was achieved by using Mn(6mes) (selectivity SCO = 96.6%), whereas the photocatalytic system using Mn(4H) yielded HCOOH as the main product (SHCOOH = 74.6%) with CO and H2 as minor products (SCO = 23.7%, SH2 = 1.7%). In these photocatalytic reactions, CuPS played its role as an efficient and very durable redox photosensitizer, while remaining stable in the reaction solution even after a turnover number of 200 had been reached (the catalyst used had a turnover number of over 1000).

Organocatalyzed Reduction of Tertiary Phosphine Oxides

Schirmer, Marie-Luis,Jopp, Stefan,Holz, Jens,Spannenberg, Anke,Werner, Thomas

supporting information, p. 26 - 29 (2016/01/25)

A novel selective catalytic reduction method of tertiary phosphine oxides to the corresponding phosphines has been developed. Notably, the reaction proceeds smoothly with low catalyst loadings of 1-5 mol% even at low temperature (70 C). Under the optimized conditions various phosphine oxides could be selectively reduced and the desired phosphines were usually obtained in excellent yields above 90%. Furthermore, we have developed a one-pot reaction sequence for the preparation of valuable phosphinborane adducts. Simple addition of BH3THF subsequent to the reduction step gave the desired adducts in yields up to 99%.

Direct conversion of phosphonates to phosphine oxides: An improved synthetic route to phosphines including the first synthesis of methyl JohnPhos

Kendall, Alexander J.,Salazar, Chase A.,Martino, Patrick F.,Tyler, David R.

, p. 6171 - 6178 (2015/02/19)

The synthesis of tertiary phosphine oxides from phosphonates was achieved reliably and in good to excellent yields using stoichiometric amounts of alkyl or aryl Grignard reagents and sodium trifluoromethanesulfonate (NaOTf). In the absence of the NaOTf additive, covalent coordination oligomers of magnesium and phosphorus species dominate the reaction, producing very low yields of phosphine oxide, but high conversions of the phosphonate starting material. Mechanistic studies revealed that a five-coordinate phosphorus species - not a phosphinate - is the reaction intermediate. A diverse array of phosphonates was converted to phosphine oxides using a variety of Grignard reagents for direct carbon-phosphorus functionalization. This new methodology especially simplifies the synthesis of dimethylphosphino (RPMe2)-type phosphines by using air-, water-, and silica-stable intermediates. To highlight this reaction, a new Buchwald-type ligand ([1,1′-biphenyl]-2-yldimethylphosphine, or methyl JohnPhos) and a classic bidentate phosphine, bis(diphenylphosphino)propane (dppp), were synthesized in excellent yields.

General and selective copper-catalyzed reduction of tertiary and secondary phosphine oxides: Convenient synthesis of phosphines

Li, Yuehui,Das, Shoubhik,Zhou, Shaolin,Junge, Kathrin,Beller, Matthias

supporting information; experimental part, p. 9727 - 9732 (2012/07/14)

Novel catalytic reductions of tertiary and secondary phosphine oxides to phosphines have been developed. Using tetramethyldisiloxane (TMDS) as a mild reducing agent in the presence of copper complexes, PO bonds are selectively reduced in the presence of other reducible functional groups (FGs) such as ketones, esters, and olefins. Based on this transformation, an efficient one pot reduction/phosphination domino sequence allows for the synthesis of a variety of functionalized aromatic and aliphatic phosphines in good yields.

Highly chemoselective metal-free reduction of phosphine oxides to phosphines

Li, Yuehui,Lu, Liang-Qiu,Das, Shoubhik,Pisiewicz, Sabine,Junge, Kathrin,Beller, Matthias

, p. 18325 - 18329 (2013/01/15)

Unprecedented chemoselective reductions of phosphine oxides to phosphines proceed smoothly in the presence of catalytic amounts of specific Br?nsted acids. By utilizing inexpensive silanes, e.g., PMHS or (EtO)2MeSiH, other reducible functional groups such as ketones, aldehydes, olefins, nitriles, and esters are well-tolerated under optimized conditions.

Reduction of phosphine oxides to phosphines with the InBr3/TMDS system

Pehlivan, Leyla,Métay, Estelle,Delbrayelle, Dominique,Mignani, Gérard,Lemaire, Marc

supporting information; experimental part, p. 3151 - 3155 (2012/05/31)

An efficient method for the reduction of phosphine oxide derivatives into their corresponding phosphines is described. The system InBr3/TMDS allows the reduction of different secondary and tertiary phosphine oxides as well as aliphatic and aromatic phosphine oxides.

The synthesis and deep purification of GaEt3. Reversible complexation of adducts MAlk3 (M = Al, Ga, In; Alk = Me, Et) with phenylphosphines

Shatunov,Korlyukov,Lebedev,Sheludyakov,Kozyrkin,Orlov, V.Yu.

experimental part, p. 2238 - 2251 (2011/06/22)

Optimal parameters of organomagnesium technique of synthesis of triethylgallium have been defined. Various techniques of deep purification of triethylgallium to the extent required in metalorganic vapor-phase epitaxy MOVPE have been studied: by way of residue ether displacement through high-performance rectification and interaction with high pure aluminum and gallium trichloride, and by way of reversible complexation with triphenylphosphine, 1,3-bis(diphenylphosphine)propane and 1,5- bis(diphenylphosphine)pentane. Advantages and disadvantages of each technique have been identified. We have shown high performance of adduct purification technique covering trimethyl and triethyl derivatives of aluminum, gallium and indium. The structure of donor-acceptor complexes between metal alkyls and the above-mentioned phosphines have been verified using H and 31P NMR spectroscopy and X-ray studies, as well as quantum chemical calculations. Thermal stability of triethylgallium and oxidation of its adducts with phosphines have been studied.

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