Phosphine Ligands

Transition-metal-catalyzed cross-coupling is an efficient tool for constructing C-C, C-N and C-O bonds in organic synthesis. Intensive interest has been focused on the development of the most effective ligands that improve catalyst performance. Ligands play a key role in stabilizing and activating the central metal atom and fine-tuning the selectivity of transformation. Phosphines have proven to be the most significant class of ligands for cross couplings, such as Negishi, Suzuki, Stille, Heck, Sonogashira, and Buchwald-Hartwig cross-coupling.

Sigma-Aldrich provides the following Phosphine Ligand Application Guide, detailing product applications to cross-coupling reactions.
Phosphine Ligand Application Guide
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761370 (Acetonitrile)[2-(dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl] gold(I) hexafluoroantimonate C37H56AuF6NO2PSb
336874 Allyldiphenylphosphine 95% C15H15P
748196 (1R,2R)-2-Amino-1-phenylpropyldiphenylphosphine C21H22NP
749494 (2-Ammonioethyl)di-tert-butylphosphonium bis(tetrafluoroborate) 96% C10H26B2F8NP
749508 (2-Ammonioethyl)diisopropylphosphonium bis(tetrafluoroborate) 97% C8H22B2F8NP
750204 (3-Ammoniopropyl)di-tert-butylphosphonium bis(tetrafluoroborate) 96% C11H28B2F8NP
750212 (3-Ammoniopropyl)diisopropylphosphonium bis(tetrafluoroborate) C9H24B2F8NP
677264 APhos 95% C16H28NP
487546 Benzyldiphenylphosphine C19H17P
84795 Benzyldiphenylphosphine, polymer-bound 200-400 mesh, extent of labeling: ~2.5 mmol/g loading  
767689 (2-Biphenyl)di-1-adamantylphosphine 97% C32H39P
900268 Bis(3,5-bis(trifluoromethyl)phenyl)(2′,6′-bis(isopropoxy)-3,6-dimethoxybiphenyl-2-yl)phosphine ≥95% C36H31F12O4P
681555 1-[2-[Bis(tert-butyl)phosphino]phenyl]-3,5-diphenyl-1H-pyrazole 96% C29H33N2P
739049 Bis[2-(diadamantylphosphino)ethyl]amine 97% C44H69NP2
745324 Bis(5H-dibenzo[a,d]cyclohepten-5-yl)phenylphosphine ≥96.5% (elemental analysis) C36H27P
716650 2-[Bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]benzaldehyde 97% C37H51O3P
736589 2,6-Bis(di-tert-butylphosphinomethyl)pyridine C23H43NP2
718122 Bis(dicyclohexylphosphinophenyl) ether 97% C36H52OP2
554707 Bis(diethylamino)phenylphosphine 97% C14H25N2P
708275 1,3-Bis-(2,6-diisopropylphenyl)-[1,3,2]diazaphospholidine 2-oxide 97% C26H39N2OP
750654 Bis(dimethylamino)chlorophosphine 96% C4H12ClN2P
716642 2-[Bis(3,5-dimethylphenyl)phosphino]benzaldehyde 97% C23H23OP
CDS020234 2,2′-Bis(diphenylphosphino)-1,1′-biphenyl AldrichCPR C36H28P2
454141 Bis(4-fluorophenyl)phenylphosphine oxide 97% C18H13F2OP
50476 Bis[4-(3,3,4,4,5,5,5-heptafluoro-2,2-bis(trifluoromethyl)pentyl)phenyl]phenylphosphine ≥90.0% C32H17F26P
710466 Bis(2-methoxyphenyl)phosphine 97% C14H15O2P
16367 Bis[4-(1H,1H,2H,2H-perfluorodecyl)phenyl]phenylphosphine ≥95% (GC) C38H21F34P
567159 1,1′-Bis(phenylphosphinidene)ferrocene 97% C16H13FeP
698539 Bis(p-sulfonatophenyl)phenylphosphine dihydrate dipotassium salt 97% C18H13K2O6PS2 · 2H2O
741248 Bis(triphenylphosphine)palladium(II) dichloride ≥99.99% trace metals basis C36H30Cl2P2Pd
739006 (2-Bromophenyl)dicyclohexylphosphine 97% C18H26BrP
698482 (2-Bromophenyl)diphenylphosphine 97% C18H14BrP
651605 tert-Butyldicyclohexylphosphine 97% C16H31P
729337 tert-Butyldicyclohexylphosphonium tetrafluoroborate 97% C16H32BF4P
639346 tert-Butyldiisopropylphosphine 97% C10H23P
591688 tert-Butyldiphenylphosphine 97% C16H19P
693383 cBRIDP Green Alternative C24H33P
694207 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine C26H38ClN2P
759171 CPhos 98% C28H41N2P
702951 Cy-cBRIDP 97% C28H37P
510742 Cyclohexyldiphenylphosphine C18H21P
702943 Cy-vBRIDP C27H35P
751413 Di(1-adamantyl)-2-dimethylaminophenylphosphine 98% C28H40NP
695823 Di-1-adamantylphosphine 97% C20H31P
772976 Di(1-adamantyl)-(2-triisopropylsiloxyphenyl)phosphine 97% C35H55OPSi
745219 (5H-Dibenzo[a,d]cyclohepten-5-yl)diphenylphosphine ≥96.5% (elemental analysis) C27H21P
CDS010222 (R)-(-)-1-[(S)-2-(di(3,5-bis-trifluoromethylphenyl)phosphino)ferrocenyl]ethyldicyclohexylphosphine AldrichCPR C40H40F12FeP2
CDS010221 (R)-(-)-1-[(S)-2-(di(3,5-bis-trifluoromethylphenyl)phosphino)ferrocenyl]ethyldi(3,5-dimethylphenyl)phosphine AldrichCPR C44H36F12FeP2
698288 Di-tert-butylcyclohexylphosphine 95% C14H29P
419362 Di-tert-butyl N,N-diisopropylphosphoramidite 95% C14H32NO2P
642629 Di-tert-butylmethylphosphine 97% C9H21P
643777 Di-tert-butyl(methyl)phosphonium tetrafluoroborate 97% C9H22BF4P
653101 Di-tert-butyl(methyl)phosphonium tetrafluoroborate 97% C9H22BF4P
676187 Di-tert-butylneopentylphosphine 95% C13H29P
676179 Di-tert-butylneopentylphosphonium tetrafluoroborate 95% C13H30BF4P
682411 Di-tert-butylphenylphosphine 95% C14H23P
41632 Dibutylphenylphosphine polymer-bound 2.8-3.8 mmol/g loading  
762245 Di-tert-butylphosphate potassium salt C8H18KO4P
734071 Di-tert-butylphosphine oxide C8H19OP
706019 2′-(Di-tert-butylphosphino)acetophenone ethylene ketal 97% C18H29O2P
774758 2-(Di-tert-butylphosphino)dimethylaminobenzene 97% C16H28NP
748358 2-(Di-tert-butylphosphino)ethylamine 10 wt. % in THF C10H24NP
701920 2-((Di-tert-butylphosphinomethyl)-6-diethylaminomethyl)pyridine C19H35N2P
710598 5-(Di-tert-butylphosphino)-1-(naphthalen-1-yl)-1H-pyrazole 97% C21H27N2P
676632 5-(Di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole 97% C32H35N4P
707694 3-(Di-tert-butylphosphonium)propane sulfonate 97% C11H25O3PS
742651 P,P-Dichloroferrocenylphosphine ≥95% (T) C10H9Cl2FeP
698814 Dicyclohexyl-(2,6-diisopropylphenyl)phosphine 97% C24H39P
692689 Dicyclohexyl(4-(N,N-dimethylamino)phenyl)phosphine 95% C20H32NP
695920 Dicyclohexyl(ethyl)phosphine C14H27P
710970 Dicyclohexyl(4-isopropylphenyl)phosphine C21H33P
651885 Dicyclohexyl(2-methylphenyl)phosphine 95% C19H29P
288284 Dicyclohexylphenylphosphine 95% C18H27P
675709 2′-(Dicyclohexylphosphino)acetophenone ethylene ketal 97% C22H33O2P
697532 2-(Dicyclohexylphosphino)benzophenone 95% C25H31OP
763365 2-(Dicyclohexylphosphino)-N,N-diisopropyl-1H-indole-1-carboxamide 97% C27H41N2OP
703060 N-(Dicyclohexylphosphino)-2-(2′-methoxyphenyl)indole 97% C27H34NOP
745359 2-[(Dicyclohexylphosphino)methyl]-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethylimidazolium iodide ≥95% (elemental analysis) C42H64IN2P
655406 2-(2-Dicyclohexylphosphinophenyl)-1,3-dioxolane 97% C21H31O2P
752231 2-[2-(Dicyclohexylphosphino)phenyl]-N-methylindole 97% C27H34NP
700711 N-(Dicyclohexylphosphino)-2-(2′-tolyl)indole 95% C27H34NP
738611 5-(Dicyclohexylphosphino)-1′,3′,5′-triphenyl-1′H-[1,4′]bipyrazole 97% C36H39N4P
651877 Dicyclohexyl(2,4,6-trimethylphenyl)phosphine 97% C21H33P
381241 Diethylphenylphosphine 96% C10H15P
731366 Diethylphosphine 98% C4H11P
747270 4-(Diethylphosphino)-N,N-dimethylaniline 97% C12H20NP
771333 Diethyl 4-(trifluoromethyl)benzylphosphonate 97% C12H16F3O3P
754536 9-[2-(Diisopropylphosphino)phenyl]-9H-carbazole 97% C24H26NP
766437 2-[Di(2-methoxyphenyl)phosphino]benzenesulfonic acid 97% C20H19O5PS
771120 Dimethylaminophenylchlorophosphine 95% C8H11ClNP
395021 4-(Dimethylamino)phenyldiphenylphosphine 95% C20H20NP
344109 (R)-(−)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine 95% C26H28FeNP
265020 Dimethylphenylphosphine 99% C8H11P
670103 2-(1,1-Dimethylpropyl)-6-(diphenylphosphino)pyridine ≥98.0% (HPLC) C22H24NP
CDS008430 (S)-(+)-(3,5-dioxa-4-phospha-cyclohepta[2,1-a:3,4-a′]dinaphthalen-4-yl)bis[(1R)-1-phenylethyl]amine, dichloromethane adduct AldrichCPR C37H32Cl2NO2P
287865 Diphenyl(2-methoxyphenyl)phosphine 98% C19H17OP
638013 4-Diphenylphosphanylbenzoic acid, 2-(trimethylsilyl)ethyl ester solution 0.5 M in THF C24H27O2PSi
326208 2-(Diphenylphosphino)benzaldehyde 97% C19H15OP
720046 2-(Diphenylphosphino)benzaldehyde oxime 97% C19H16NOP
43151 3-(Diphenylphosphino)benzenesulfonic acid sodium salt technical, ≥90% (31P-NMR) C18H14NaO3PS
454885 2-(Diphenylphosphino)benzoic acid 97% C19H15O2P
401595 4-(Diphenylphosphino)benzoic acid 97% C19H15O2P
720038 N-[2-(Diphenylphosphino)benzylidene]cyclohexylamine 97% C25H26NP
748315 (1R,2R)-2-(Diphenylphosphino)cyclohexylamine 95% C18H22NP
768065 2-(Diphenylphosphino)-N,N-dimethylbenzylamine 95% C21H22NP
749516 2-(Diphenylphosphino)ethanaminium tetrafluoroborate 96% C14H17BF4NP
43162 2-(Diphenylphosphino)ethylamine ≥95.0% (GC) C14H16NP
538019 2-Diphenylphosphinoethyl-functionalized silica gel 200-400 mesh, extent of labeling: 0.7 mmol/g loading  
695599 2-(2-(Diphenylphosphino)ethyl)pyridine kanata purity C19H18NP
748366 (R)-1-(Diphenylphosphino)-3-methyl-2-butylamine 97% C17H22NP
748277 (S)-1-(Diphenylphosphino)-3-methyl-2-butylamine 97% C17H22NP
CDS010477 (R)-(+)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline AldrichCPR C31H22NP
779911 (RS)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline 95% C31H22NP
750174 3-(Diphenylphosphino)propan-1-aminium tetrafluoroborate 95% C15H19BF4NP
43163 3-(Diphenylphosphino)-1-propylamine technical, ≥90% (GC) C15H18NP
708127 4-(Diphenylphosphino)styrene 97% C20H17P
768081 2-(Diphenylphosphino)-N,N,N-trimethylbenzylammonium triflate 96% C23H25F3NO3PS
392960 Diphenyl-2-pyridylphosphine 97% C17H14NP
287938 Diphenyl(o-tolyl)phosphine 98% C19H17P
155039 Diphenyl(p-tolyl)phosphine 96% C19H17P
252972 Diphenylvinylphosphine 95% C14H13P
716626 2-(Di-p-tolylphosphino)benzaldehyde 97% C21H19OP
336904 Ethyldiphenylphosphine 98% C14H15P
454419 Ethyldiphenylphosphine oxide 97% C14H15OP
808423 HandaPhos toluene solution (14 mg HandaPhos per 1 mL of toluene)  
799580   HandaPhos ≥95% C35H47O3P
07026 [4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluorodecyl)phenyl] diphenylphosphine ≥99% C28H18F17P
567728 (4-Hydroxyphenyl)diphenylphosphine 98% C18H15OP
596736 (4-Hydroxyphenyl)diphenylphosphine, polymer-bound 50-100 mesh, extent of labeling: 1.5-2.0 mmol/g P loading, 1 % cross-linked with divinylbenzene  
760609 Isocyanatophosphonic dichloride 95% CCl2NO2P
336920 Isopropyldiphenylphosphine 97% C15H17P
533416 JandaJel-triphenylphosphine 50-100 mesh, extent of labeling: ~3.0 mmol/g P loading, 2 % cross-linked  
727385   Metal frame for glass microreactor 43738 with rod  
43115 (Methoxymethyl)diphenylphosphine oxide purum, ≥97.0% (CH) C14H15O2P
454087 (Methoxymethyl)diphenylphosphine oxide 98% C14H15O2P
763241 1-Methyl-2-(2-dicyclohexylphosphinophenyl)-1H-benzoimidazole 95% C26H33N2P
762954 1-Methyl-2-(2-diisopropylphosphinophenyl)-1H-benzoimidazole 97% C20H25N2P
244902 Methyldiphenylphosphine 99% C13H13P
454427 Methyldiphenylphosphine oxide 98% C13H13OP
763268 1-Methyl-2-(2-diphenylphosphinophenyl)-1H-benzoimidazole 95% C26H21N2P
751618 MorDalphos 97% C30H42NOP
775681 OTPP  
900593 PAd-DalPhos 95% C30H34O3P2
675784 1,2,3,4,5-Pentaphenyl-1′-(di-tert-butylphosphino)ferrocene C48H47FeP
762687 Pentathiodiphosphorus(V) acid-P,P′-bis(pyridinium betaine) C10H10N2P2S5
19971 Phenylbis[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phenyl]phosphine ≥90.0% C34H21F26P
89753   Phenyldi(o-tolyl)phosphine polymer-bound extent of labeling: ~2.2 mmol/g loading  
674389 Phenylphosphine ca. 10% weight in hexanes C6H7P
479497 4,4′-(Phenylphosphinidene)bis(benzenesulfonic acid) dipotassium salt hydrate 97% C18H13K2O6PS2 · xH2O
659940 Phosphine Ligands Kit I  
654132 Poly(ethylene glycol) di-(4-hydroxyphenyl)diphenylphosphine extent of labeling: 0.5-1.0 mmol/g P loading  
532649 Poly(ethylene glycol) triphenylphosphine  
761419 (R)-(4,4′,6,6′-Tetramethoxybiphenyl-2,2′-diyl)bis(bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine 97% C76H108O8P2
761400 (S)-(4,4′,6,6′-Tetramethoxybiphenyl-2,2′-diyl)bis(bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine 97% C76H108O8P2
761389 (R)-(4,4′,6,6′-Tetramethoxybiphenyl-2,2′-diyl)bis(bis(3,5-dimethylphenyl)phosphine) 97% C48H52O4P2
761397 (S)-(4,4′,6,6′-Tetramethoxybiphenyl -2,2′-diyl)bis(bis(3,5-dimethylphenyl )phosphine) 97% C48H52O4P2
686344 4,4,5,5-Tetramethyl-1,3,2-dioxaphospholane 2-oxide 95% C6H13O3P
695459 1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane 97% C16H21O3P
804428 Tetrapropylphosphonium bromide 95% C12H28BrP
336939 Triallylphosphine 95% C9H15P
695467 1,3,5-Triaza-7-phosphaadamantane 97% C6H12N3P
336947 Tribenzylphosphine 98% C21H21P
247049 Tributylphosphine mixture of isomers, 97% C12H27P
90827 Tributylphosphine ≥93.5% (Tri-N-butylphosphine, GC) C12H27P
T49484 Tri-n-butylphosphine 97% C12H27P
731374 Tri-n-butylphosphine 99% C12H27P
570958 Tri-tert-butylphosphine 98% C12H27P
336955 Tri-tert-butylphosphine 90%, technical grade C12H27P
655325 Tri-tert-butylphosphine solution 1.0 M in toluene C12H27P
172766 Tributylphosphine oxide 95% C12H27OP
576492 Tributylphosphine tetrafluoroborate 97% C12H28BF4P
578940 Tri-tert-butylphosphonium tetrafluoroborate 97% C12H28BF4P
261971 Tricyclohexylphosphine C18H33P
592285 Tricyclohexylphosphine solution 1 M in toluene C18H33P
455164 Tricyclohexylphosphine solution 20 wt. % in toluene C18H33P
631493 Tricyclohexylphosphine tetrafluoroborate 97% C18H33P · HBF4
649074 Tricyclopentylphosphine 97% C15H27P
673951 Tricyclopentylphosphine tetrafluoroborate 95% Green Alternative C15H28BF4P
90535 Triethylphosphine ≥97.0% C6H15P
245275 Triethylphosphine 99% C6H15P
346179 Triethylphosphine solution 1.0 M in THF C6H15P
562394 Triethylphosphine oxide 97% C6H15OP
695246 ((4-Trifluoromethyl)phenyl)di-tert-butylphosphine technical grade, 85% C15H22F3P
383767 Tri(2-furyl)phosphine 99% C12H9O3P
701289 ((2,4,6-Tri-isopropyl)phenyl)di-cyclohexylphosphine 97% C27H45P
377309 Triisopropylphosphine technical grade C9H21P
698466 Triisopropylphosphonium tetrafluoroborate 97% C9H22BF4P
323322 Trimethylphosphine 97% C3H9P
324108 Trimethylphosphine solution 1.0 M in THF C3H9P
324116 Trimethylphosphine solution 1.0 M in toluene C3H9P
710946 Trimethylphosphonium tetrafluoroborate 98% C3H10BF4P
667218 Tri-1-naphthylphosphine 97% C30H21P
117854 Trioctylphosphine technical grade, 90% C24H51P
92840 Trioctylphosphine technical, ~90% (GC) C24H51P
718165 Trioctylphosphine 97% C24H51P
223301 Trioctylphosphine oxide ReagentPlus®, 99% C24H51OP
00676 Trioctylphosphine oxide for extraction analysis, ≥98.5% C24H51OP
346187 Trioctylphosphine oxide technical grade, 90% C24H51OP
93092 Triphenylphosphine ≥95.0% (GC) C18H15P
T84409 Triphenylphosphine ReagentPlus®, 99% C18H15P
14664 Triphenylphosphine, polymer-bound 100-200 mesh, extent of labeling: ~3.2 mmol/g loading C18H15P
93093 Triphenylphosphine, polymer-bound 100-200 mesh, extent of labeling: ~3 mmol/g triphenylphosphine loading C18H15P
366455 Triphenylphosphine, polymer-bound 100-200 mesh, extent of labeling: ~3.0 mmol/g loading, 2 % cross-linked with divinylbenzene C18H15P
93094 Triphenylphosphine, polymer-bound 100-200 mesh, extent of labeling: ~1.6 mmol/g loading C18H15P
93098 Triphenylphosphine hydrobromide purum, ≥96.0% (T) C18H16BrP
338389 Triphenylphosphine hydrobromide 97% C18H16BrP
SYX00009 Triphenylphosphineimine hemisulfate salt AldrichCPR C18H16NP · 0.5 H2SO4
T84603 Triphenylphosphine oxide 98% C18H15OP
655430 Triphenylphosphine oxide, polymer-bound 200-400 mesh particle size, extent of labeling: 2.5-3.0 mmol/g P loading, 2 % cross-linked with divinylbenzene  
689602 4-(Triphenylphosphonio)butane-1-sulfonate 99% C22H23O3PS
336971 Tripropylphosphine 97% C9H21P
74231 Tris[3,5-bis(trifluoromethyl)phenyl]phosphine ≥95.0% (GC), yellow-brown C24H9F18P
249491 Tris(4-chlorophenyl)phosphine 95% C18H12Cl3P
253189 Tris(diethylamino)phosphine 97% C12H30N3P
393436 Tris(2,6-dimethoxyphenyl)phosphine 98% C24H27O6P
93338 Tris(dimethylamino)phosphine purum, ≥97.0% (GC) C6H18N3P
393290 Tris(dimethylamino)phosphine 97% C6H18N3P
698253 Tris(3,5-dimethylphenyl)phosphine 96% C24H27P
CDS006812 Tris(2,4-dimethyl-5-sulfanatophenyl)phosphine trisodium salt AldrichCPR C24H26Na3O10PS3
327697 Tris[2-(diphenylphosphino)ethyl]phosphine 97% Green Alternative C42H42P4
77965 Tris(2-ethylhexyl)phosphine oxide Selectophore, ≥95.0% C24H51OP
395099 Tris(4-fluorophenyl)phosphine 98% Green Alternative C18H12F3P
07086 Tris[4-(heptadecafluorooctyl)phenyl]phosphine ≥85% C42H12F51P
177881 Tris(hydroxymethyl)phosphine 90% C3H9O3P
698261 Tris(4-methoxy-3,5-dimethylphenyl)phosphine 97% C27H33O3P
710563 Tris(o-methoxyphenyl)phosphine 96% C21H21O3P
395102 Tris(4-methoxyphenyl)phosphine 95% C21H21O3P
775452 Tris(4-methyl-1-piperazinyl)phosphine 97% C15H33N6P
290572 Tris(pentafluorophenyl)phosphine 97% C18F15P
775444 Tris(1-pyrrolidinyl)phosphine 97% C12H24N3P
12118 Tris[4-(tridecafluorohexyl)phenyl]phosphine ≥90% C36H12F39P
49317 Tris[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phenyl]phosphine >90.0% C42H24F39P
666629 Tris(4-trifluoromethylphenyl)phosphine 97% C21H12F9P
392081 Tris(2,4,6-trimethoxyphenyl)phosphine C27H33O9P
395080 Tris(2,4,6-trimethylphenyl)phosphine 97% C27H33P
333670 Tris(trimethylsilyl)phosphine 95% C9H27PSi3
287822 Tri(o-tolyl)phosphine 97% C21H21P
287830 Tri(p-tolyl)phosphine 98% C21H21P
704903 Tri-o-tolylphosphine tetrafluoroborate C21H22BF4P
710342 TrixiePhos 97% C28H31P
711179 vBRIDP 97% C23H31P