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1,4-Bis(diphenylphosphino)butane
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Chemical compound
Dppb.svg (Butane-1,4-diyl)bis(diphenylphosphane) dppb, dpb 7688-25-7 82124 35HP6LTD2D 231-698-7 71648 74118 1S/C28H28P2/c1-5-15-25(16-6-1)29(26-17-7-2-8-18-26)23-13-14-24-30(27-19-9-3-10-20-27)28-21-11-4-12-22-28/h1-12,15-22H,13-14,23-24H2 BCJVBDBJSMFBRW-UHFFFAOYSA-N C1=CC=C(C=C1)P(CCCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
28 28 2 132-136
07 Warning 302 315 319 335 261 264 270 271 272 273 280 301+312 302+352 304+340 305+351+338 312 321 330 332+313 333+313 337+313 362 363 391 403+233 405 501
1,4-Bis(diphenylphosphino)butane (dppb) is an organophosphorus compound with the formula (Ph2PCH2CH2)2. It is less commonly used in coordination chemistry than other diphosphine ligands such as dppe. It is a white solid that is soluble in organic solvents.
Coordination complexes
Nickel complexes in which the ligand is bidentateNeary Michelle C. Quinlivan Patrick J. Parkin Gerard Zerovalent Nickel Compounds Supported by 1,2-Bis(diphenylphosphino)benzene: Synthesis, Structures, and Catalytic Properties Inorganic Chemistry 15 December 2017 57 1 374–391 10.1021/acs.inorgchem.7b02636 29244503 Nwokogu Godson C. Cytarska Joanna Zaidlewicz Marek Dichloro[1,4-bis(diphenylphosphino)butane]nickel(II) Encyclopedia of Reagents for Organic Synthesis 15 October 2005 10.1002/047084289x.rd095.pub2 John Wiley & Sons, Ltd en 0471936235 or monodentateCorain B. Bressan M. Favero G. The reactions of Ni(O) phosphino complexes with carbon monoxide Inorganic and Nuclear Chemistry Letters February 1971 7 2 197–201 10.1016/0020-1650(71)80151-4 are known.
Palladium complexes containing dppb are used in a variety of catalytic reactions.Nozaki Kyoko Sato Naomasa Takaya Hidemasa Acylcyanation of Terminal Acetylenes: Palladium-Catalyzed Addition of Aryloyl Cyanides to Arylacetylenes The Journal of Organic Chemistry May 1994 59 10 2679–2681 10.1021/jo00089a006Minato Akio Suzuki Keizo Tamao Kohei Kumada Makoto Mixed heteroarene oligomers Journal of the Chemical Society, Chemical Communications 1984 8 511 10.1039/C39840000511
The ligand's natural bite angle is 94° in its bidentate coordination mode.Birkholz (née Gensow) Mandy-Nicole Freixa Zoraida van Leeuwen Piet W. N. M. Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions Chemical Society Reviews 2009 38 4 1099–1118 10.1039/B806211K 19421583
Related compounds
1,2-Bis(dimethylphosphino)ethane
Bis(diphenylphosphino)methane
1,3-Bis(diphenylphosphino)propane
References
Category:Chelating agents
Category:Diphosphines
Category:Phenyl compounds
Category:1,4-Butanediyl compounds