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Buchwald–Hartwig 偶聯(lián)反應(yīng)是鈀催化和堿存在下胺與鹵代芳香化合物的交叉偶聯(lián)反應(yīng)。是合成芳胺化合物的重要方法。百靈威可提供種類齊全的Buchwald–Hartwig 偶聯(lián)反應(yīng)相關(guān)試劑，并備有充足現(xiàn)貨。

◆ 發(fā)展歷程

Buchwald–Hartwig 這一類型的反應(yīng)最早是由烏克蘭的 Lev M. Yagupolskii 等在 1986 年發(fā)現(xiàn)的。此后美國的 Buchwald 和 Hartwig 兩個團隊又分別在 1994 年重新發(fā)現(xiàn)這個反應(yīng)。耶魯大學(xué)的 Hartwig 等用的是對溴甲苯與三丁基錫基胺之間的偶聯(lián)。[1]

麻省理工學(xué)院的 Buchwald 等用的則是間溴苯甲醚與另一三丁基錫胺之間的偶聯(lián)，見下：[2]

其后又發(fā)展了第二代的 Buchwald–Hartwig 反應(yīng)，即用游離胺和強堿，代替最早使用的氨基錫烷。[3]

此外，反應(yīng)中的芳鹵也可為擬芳鹵三氟甲磺酸的酚酯所代替，胺可為伯胺或仲胺，胺上的取代基可以為任何有機基團。鈀催化劑常為鈀磷配合物，如四( 三苯基膦) 鈀，也可為三( 雙亞芐基丙酮)二鈀［4］等其他鈀配合物。反應(yīng)用堿一般為雙( 三甲硅基)氨基鈉或叔丁醇鹽。

◆ 相關(guān)產(chǎn)品

產(chǎn)品編號
名稱與規(guī)則
包裝*
目錄價*
Tris(dibenzylideneacetone)dipalladium(0)
三(雙亞芐基丙酮)雙鈀
500mg
745
1g
845
1,1'-Bis(diphenylphosphino)ferrocene palladium(II)chloride
1,1'-雙(二苯膦基)二茂鐵二氯化鈀(II)二氯甲烷復(fù)合物
1g
270
5g
1013
411434
46-0400
Dichlorobis(benzonitrile)palladium (II)
二(苯腈)二氯化鈀(II)
250 mg
200
1g
545
5g
2043
46-1780
46-1781
Palladium(II) acetate
乙酸鈀
1g
873
2g
1616
5g
2820
182482
46-2150
Tetrakis(triphenylphosphine)palladium(0)
四(三苯基膦)鈀
1g
200
5g
745
25g
2800
205985
26-0270
1,1'-Bis(diphenylphosphino)ferrocene DPPF
1,1'-雙(二苯基膦)二茂鐵
1g
234
5g
518
25g
1943
102357
15-8050
Tri-o-tolylphosphine
三(鄰-甲苯基)膦
1g
200
5g
400
25g
980
2-(Di-t-butylphosphino)biphenyl,99%JohnPhos
2-（二叔丁基磷）聯(lián)苯
500mg
585
2g
1755
2-(Dicyclohexylphosphino)biphenyl
2-（二環(huán)己基磷）聯(lián)苯
500mg
345
2g
1035
2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl
2-二環(huán)己基磷-2-（N,N-二甲基氨基）聯(lián)苯
500mg
600
2g
1800
1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
1,3-雙(2,4,6-三甲基苯基)氯化咪唑
1g
690
5g
2760

*包裝：僅列出部分包裝，更多包裝情況請聯(lián)系百靈威。
*目錄價：價格供參考，購買前請聯(lián)系百靈威核實銷售價格。

◆ 參考資料

1.Frederic Paul, Joe Patt, John F. Hartwig (1994), "Palladium-catalyzed formation of carbon-nitrogen bonds. Reaction intermediates and catalyst    improvements in the hetero cross-coupling of aryl halides and tin amides", J. Am. Chem.Soc. 116 (13): 5969–5970.
2.Anil S. Guram and Stephen L. Buchwald (1994), "Palladium-Catalyzed Aromatic Aminations with in situ Generated Aminostannanes", J.    Am. Chem. Soc. 116 (17): 7901–7902.
3.Janis Louie and John F. Hartwig (1995), "Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in    the absence of tin reagents", Tetrahedron Letters 36 (21): 3609–3612.
4.John P. Wolfe and Stephen L. Buchwald (2004). "Palladium-Catalyzed Amination Of Aryl Halides And Aryl Triflates". Org. Synth.; Coll. Vol.    10: 423.

 ◆ 最新產(chǎn)品

Buchwald Biaryl Phosphine Ligand Kit
for Aromatic Carbon-Heteroatom Formation, Suzuki Coupling and Negishi Cross-coupling


Buchwald Biaryl Phosphine Ligand Kit for Aromatic Carbon-Heteroatom Formation, Suzuki Coupling and Negishi Cross-coupling Contains the smallest unit size of the sixteen compounds listed                                           1 kit
racemic-2-Di-t-butylphosphino-1,1'-binaphthyl, 98% [255836-67-0] P; FW: 398.53; white xtl.; m.p. 147-149
250mg
1g
Technical Notes:
1. Ligand for the Pd-catalyzed formation of oxygen heterocycles.
2. Ligand for the intermolecular Pd-catalyzed synthesis of aryl ethers.
3. Ligand for the intramolecular Pd-catalyzed synthesis of aryl ethers.
4. Ligand for the synthesis of carbazoles by Pd-catalyzed double N-arylation reaction.
5. Ligand fo the Pd-catalyzed cyanation of (hetero)arylchlorides.

References:
1. J. Am. Chem. Soc., 2000, 122, 12907.
2. J. Am. Chem. Soc., 2001, 123, 10770.
3. J. Am. Chem. Soc., 2001, 123, 12202.
4, Tetrahedron, 2006, 62, 6792.
5. Org. Lett., 2007, 9, 1711.
2-(Di-t-butylphosphino)biphenyl, 99% JohnPhos [224311-51-7] C20H27P; FW: 298.41; colorless xtl.; m.p. 85/
500mg 10g
2g      50g
Technical Notes:
1. Ligand used in the palladium-catalyzed synthesis of aromatic amines from aryl chlorides, bromides and triflates.
2. Ligand employed in a very active and general catalyst for Suzuki coupling reactions using aryl chlorides,bromides        and triflates.
3. Ligand for the palladium-catalyzed formation of diarylethers from aryl chlorides and bromides.
4. Ligand used in palladium-catalyzed synthesis of oxindoles from " -chloroacetanilides.
5. Effective ligand used in palladium-catalyzed arylation of thiazoles.
6. Used in the formation of 2-benzylindolines via sequential palladium-catalyzed N-arylation/cyclization/C-arylation.
7. Selective in the palladium-catalyzed arylation of silyl enol ethers formed from copper-catalyzed reduction of enones.
8. Ligand used in the palladium-catalyzed vinylation of aryl bromides.
9. Ligand used in the platinum-catalyzed synthesis of indolizinones.
10. Ligand used in the palladium-catalyzed diarylation of thiophenes.
11. Ligand used in the amination of vinyl halides by carbazates.
12. Ligand used in the regeioselective synthesis of 2,4-disubstituted syloles.



References:
1. Angew. Chem. Int. Ed., 1999, 38, 2413.                 8. Org. Lett., 2004, 6, 4809.
2. J. Org. Chem., 2000, 65, 1158.                               9. Org. Lett., 2006, 7, 63.
3. J. Am. Chem. Soc., 1999, 121, 9550.                     10.Org. Lett., 2007, 9, 1169.
4. J. Am. Chem. Soc., 1999, 121, 4369.                     11.J. Org. Chem., 2006, 71, 8309.
5. J. Am. Chem. Soc., 2003, 125, 12084.                   12. Org. Lett., 2007, 9, 275.
6. Tetrahedron, 2003, 59, 5685.                                  13. J. Am. Chem. Soc., 2008, 130, 1526.
7. J. Am. Chem. Soc., 2004, 126, 13906.
Di-t-butylphosphino-2'-(N,N-dimethylamino)biphenyl, 98% [224311-49-3]
(CH3)2NC6H4C6H4P(C4H9)2; FW: 341.47; white xtl.
500mg
2g
Technical Notes:
1. Useful ligand for Pd-catalyzed carbon-oxygen bond forming reactions.
2. Ligand used selective Pd-catalyzed arylation of ammonia.
3. Ligand used for selective Pd-catalyzed silylation of aryl chlorides.

References:
1. J. Am. Chem. Soc., 2001, 123, 12202.
2. J. Am. Chem. Soc., 2007, 129, 10354.
3. Org. Lett., 2007, 9, 3785.
2-Di-t-butylphosphino-2'-methylbiphenyl, 99% [255837-19-5]
C21H29P; FW: 312.43; white xtl.
Technical Notes:
1. Ligand used in the Pd-catalyzed arylations of malonate esters and 1,3-diketones.
2. Ligand used in the Pd-catalyzed formation of t-butyl ethers from unactivated aryl halides.
3. Ligand used in the Pd-catalyzed " -arylations of nitroalkanes.

References:
1. J. Am. Chem. Soc., 2000, 122, 1360.
2. J. Org. Chem., 2001, 66, 2498.
3. J. Org. Chem., 2002, 67, 106.
2-Di-t-butylphosphino-3,4,5,6-tetramethyl-2',4',6'-tri-i-propylbiphenyl, min. 98% [857356-94-6] C33H53P; FW: 480.75; white microxtl.; m.p. 166-168/
250mg
1g
Technical Notes:
1. Ligand for the palladium-catalyzed amidation of aryl chlorides.
2. Ligand for the palladium-catalyzed synthesis of phenols from aryl halides.
3. Ligand for the palladium-catalyzed coupling of aryl halides and secondary alcohols.

References:
1. J. Am. Chem. Soc., 2007, 129, 13001.
2. J. Am. Chem. Soc., 2006, 128, 10894.
3. J. Am. Chem. Soc., 2005, 127, 8146.
2-Di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl, min. 98% t-butylXPhos [564483-19-8] C29H45P; FW: 424.64; white xtl.; m.p. 147-149/
500mg
2g
Technical Notes:
1. Ligand for the Pd-catalyzed synthesis of phenols and aromatic ethers.
2. Ligand for the Pd-catalyzed N-arylation of aminoheterocycles.
3. Ligand for the Pd-catalyzed N-arylation of indazoles and pyrazoles.
4. Ligand for the Pd-catalyzed amination of aryl nonaflates.
5. Ligand for the Pd-catalyzed stereoselective formation of alfa-O-glycosides.
6. See 15-1149 Technical Note 3.

References:
1. J. Am. Chem. Soc., 2006, 128, 10694.                 3. J. Org. Chem., 2006, 71, 430.
2. Angew. Chem. Int. Ed., 2006, 45.                         4.O rg. Lett., 2007, 9, 3173.
2-(Dicyclohexylphosphino)biphenyl, 98% [247940-06-3] C12H9[P(C6H11)2]; FW: 350.49; white xtl.; m.p. 103/
500mg 10g
2g      50g
Technical Notes:
1. See 15-1045.
2. Ligand used in the palladium-catalyzed sy nthesis of aromatic amines from aryl chlorides, bromides and triflates.
3. Ligand employed in Suzuki coupling reactions in volving aryl chlorides, bromides and triflates.
4. Useful ligand for the Pd-catal yzed oxidation of alcohols in the presence of chlorobenzenes.
5. Useful ligand for the Pd-catalyzed amination with ammonia equivalents.
6. Ligand for the gold(I)-catalyzed intramolecular [4+2] cycl oadditions involving 1,3-enynes and arylalkynes with alkenes.
7. Ligand used in the palladium-catalyz ed borylation of aryl bromdies.
8. Ligand used in the palladium-catalyz ed siliylation of aryl chlorides.

References:
1. Angew. Chem. Int. Ed., 1999, 38, 2413.                  5. Org. Lett., 2001, 3, 3417.
2. J. Org. Chem., 2000, 65, 1158.                               6. J. Am. Chem. Soc., 2005, 127, 6178.
3. J. Am. Chem. Soc., 1999, 121, 9550.                     7. Helv. Chim. Acta., 2006, 89, 936.
4. Org. Lett., 2003, 5, 2485.                                       8. Org. Lett,, 2007, 9, 3785.
2'-Dicyclohexylphosphino-2,6-dimethoxy-3-sulfonato-1,1'-biphenyl hydrate sodium salt, min. 98% C26H34NaO5PS.XH2O; FW: 512.58; light yellow solid
Note: Soluble version of 15-1143 S-Phos.
500mg
2g
Technical Note:
1. First general ligand for the Pd-catalyzed Suzuki-Miyaura coupling reaction of aryl chlorides and for the coupling of challenging substrate combinations in water.
2-Dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, min. 98% S-Phos C26H35O2P; FW: 410.53; white xtl.; m.p. 158-162/
500mg
2g
Technical Notes:
1. Ligand used in the palladium-catalyzed Suzuki-Miyaura coupling of boronic esters with heteroaryl halides.
2. Ligand used in the palladium-catalyzed Suzuki-Miyaura coupling of boronic acids with aryl halides
3. Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chloride.
4. Employed in the gold(I)-catalyzed intramolecular [4+2] cycloadditions of 1,3-enynes and arylalkynes with alkenes.
5. Effictive ligand in the palladium-catalyzed amination of heteroaryl halides.
6. Ligand employed in borylation of aryl chlorides.
7. Ligand used in palladium-catalyzed Kumada-Corriu cross coupling at low temperatures.


References:
1. J. Am. Chem. Soc., 2004, 126, 706.
2. Angew Chem. Int. Ed., 2004, 43, 1871.
3. Org. Lett., 2004, 6, 2649.
4. J. Am. Chem. Soc., 2005, 127, 6178.
5. Org. Lett., 2005, 7, 3965.
6. Angew. Chem. Int. Ed, 2007, 46, 5359.
7. J. Am. Chem. Soc., 2008, 129, 3844.
2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl, 98% DavePhos [213697-53-1]
(CH3)2NC6H4-C6H4P(C6H11)2; FW: 393.55; white xtl.; m.p.115-119/
500mg
2g
Technical Notes:
1. Ligand used in the palladium-catalyzed Suzuki coupling and amination of unactivated aryl chlorides. The reactions generally occur at room temperature and give high yields of product.
2. Ligand used in palladium-catalyzed C-N bond formation. A general synthesis of N6-aryl-2'-deoxyadenosine analogues.
3. Ligand used in palladium-catalyzed N-arylation of indoles.
4. Ligand used in palladium-catalyzed synthesis of aryl-tert-butyl ethers.
5. Effective ligand in the palladium-catalyzed arylation of ester enolates.
6. Ligand employed in arylation of ketone enolates using ortho-halo nitrobenzenes.
7. Ligand employed in the amination of aryl nonaflates using palladium catalysts.
8. Ligand used for cascade alkenyl amination/Heck reaction for the synthesis of indoles.
9. Ligand used in palladium-catalyzed Kumada-Corriu cross coupling at low temperatures.
10. Ligand used in rhodium-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines.
15-1145
(cont.)
 
2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl, 98% DavePhos [213697-53-1]

References:
1. J. Am. Chem. Soc., 1998, 120, 9722.           6. J. Am. Chem. Soc., 2002, 124, 15168.
2. J. Am. Chem. Soc., 1999, 121, 6090.           7. J. Org. Chem., 2003, 68, 9563.
3. Org. Lett., 2000, 2, 1403.                            8. Chem. Eur. J., 2005, 11, 2276.
4. J. Org. Chem., 2001, 66, 2498.                    9. J. Am. Chem. Soc., 2007, 129, 3844.
5. J. Am. Chem. Soc., 2001, 123, 7996.          10. J. Am. Chem. Soc., 2008, 130, 1570.
2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl, min. 98% RuPhos [787618-22-8]
C30H43O2P; FW: 466.64; white pwdr.; m.p. 123-124/
500mg
2g
Technical Notes:
1. Ligand used for the Pd-catalyzed Negishi cross-coupling reaction of (hetero)arylchlorides.
2. Ligand used for the Pd-catalyzed synthesis of N-aryl benzimidazoles.
3. Ligand used for the Pd-catalyzed synthesis of heteroacenes.

References:
1. J. Am. Chem. Soc., 2004, 126, 13028.
2. Angew. Chem. Int. Ed., 2007, 46, 7509.
3. J. Org. Chem., 2007, 72, 5119.
2'-Dicyclohexylphosphino-2,6-di-i-propyl-4-sulfonato-1,1'-biphenyl hydrate sodium salt [870245-84-4]
C30H42NaO3PS; FW: 536.88; white solid
500mg
2g
Technical Notes:
1. Water soluble catalyst for Sonogashira coupling reactions.
2. Water soluble catalyst for couplings of benzyl chlorides and terminal alkynes.

References:
1. Angew. Chem. Int. Ed., 2005, 44, 6173.
2. Synlett 2006, 2941.
2-Dicyclohexylphosphino-2'-methylbiphenyl, min. 98% MePhos [251320-86-2]
C25H33P; FW: 364.51; white xtl.; m.p. 107-110/
500mg
2g
Technical Notes:
1. Ligand for the Pd-catalyzed formation of " -arylketones.
2. Ligand for the Pd-catalyzed amination reaction (See 15-1045).
3. Ligand for the Pd-catalyzed hydrazone arylation.

References:
1. J. Am. Chem. Soc., 2000, 122, 1360.
2. Adv. Synth. Catal., 2005, 347, 773.
2-Dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl, min. 98% X-Phos [564483-18-7]
C33H49P; FW: 476.72; white pwdr,; m.p. 185/
500mg
2g
Technical Notes:
1. Exceptional ligand for Pd-catalyzed amination and amidation of aryl sulfonates.
2. Ligand used for the Pd-catalyzed Suzuki-Miyaura coupling reaction and carbonyl enolate coupling.
3. Ligand used for the chemoselective amination of arylchlorides.
4. Ligand used for the Pd-catalyzed borylation of aryl chlorides.
5. Ligand used for the Pd-catalyzed amination of vinyl halides and triflates.
6. Ligand used for the Pd-catalyzed three-component synthesis od indoles.

References:
1. J. Am. Chem. Soc., 2003, 125, 6653.            5. Angew. Chem. Int. Ed., 2007, 46, 5359.
2. J. Am. Chem. Soc., 2003, 125, 11818.          6. J. Org. Chem., 2005, 70, 8638.
3. Angew. Chem. Int. Ed., 2006, 45, 6523.          7. Angew. Chem. Int. Ed., 2007, 46, 1529.
4. J. Am. Chem. Soc., 2007, 129, 3358.
2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos
C35H53O2P; FW: 536.77; white xtl.; m.p. 191-193/
250mg
1g
Technical Notes:
1. Catalyst for cross-coupling reactions using aryl mesylates with electron-deficient anilines.
2. Catalyst for rapid C-N bond-forming process at low catalyst loading.

Reference:
1. J. Am. Chem. Soc., 2008, 130, 13552.
2-Diphenylphosphino-2'-(N,N-dimethylamino)biphenyl, 98% [240417-00-9]
C26H24NP; FW: 381.46; white pwdr.
500mg
2g
Technical Notes:
1. Useful ligand for sterically hindered substrates in the Pd-catalyzed amination reactions of aryl bromides.
2. Ligand employed in the coupling of enantiomerically pure cis-dimethylpiperazine with bromobenzene . Epimerization was not observed.
3. Ligand employed for the Pd-catalyzed heteroarylation of acetone.

References:
1. J. Am. Chem. Soc., 2001, 123, 1792.
2. Tetrahedron Lett., 2003, 44, 8869.

Buchwald Palladacycle Precatalyst Kit

96-5503       Buchwald Palladacycle Precatalyst Kit                                                                                               1kit
                   Contains the smallest unit of the items listed below. Components available for individual sale.

Chloro(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl] palladium(II), min. 98% C37H55ClNPPd; FW: 686.69; white pwdr.
Technical Note:
 1. See 46-0268.
100mg
500mg
Chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-bipTechnical
Note:1. See 46-0268.henyl)[2-(2-aminoethylphenyl)]palladium(II) dichloromethane adduct, min. 98% [1028206-58-7]
C34H45ClNO2PPd; FW: 672.57; white pwdr.
Technical Note:
 1. See 46-0268.
250mg
1g
Chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl] palladium(II), min. 98%
C43H63ClNO2PPd; FW: 798.81; white pwdr.
100mg
500mg
Technical Notes:
1.Catalyst for cross-coupling reactions using aryl mesylates with electron-deficient anilines.
2. Catalyst for rapid C-N bond-forming process at low catalyst loading.
Chloro(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II), methyl-t-butylether adduct, min. 98% [1028206-60-1]
C38H53ClNO2PPd; FW: 728.68; white pwdr.
Technical Note:
1. See 46-0268.
100mg
500mg
Chloro(2-dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl] palladium(II) methyl-t-butylether adduct, min. 98% [1028206-56-5]
C41H59ClNPPd; FW: 738.76; white pwdr.
250mg
1g
Technical Notes:
1. Catalyst for cross-coupling reactions of electron-deficient anilines with aryl chlorides.
2. Catalyst for rapid C-N bond-forming process at low catalyst loading.
3. Catalyst for C-N cross-coupling reactions, at or below room temperature.

Reference:
1. J. Am. Chem. Soc., 2008, 130, 6686.

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