Allyltri-n-butyltin, 97%

Name: Allyltri-n-butyltin, 97%
SKU: L14087.06

CAS: 24850-33-7 | C15H32Sn | 331.13 g/mol

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Catalog number L14087.06

also known as L14087-06

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5 g

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Specifications

Beilstein3588340

CAS24850-33-7

Chemical Name or MaterialAllyltri-n-butyltin

DOT InformationTransport Hazard Class: 6.1; Packing Group: III; Proper Shipping Name: ORGANOTIN COMPOUNDS, LIQUID, N.O.S.

Density1.079

Allyltri-n-butyltin acts as an allylation reagent for aldehydes catalyzed by chiral Lewis acids and ytterbium(III) trifluoromethanesulfonate. It is also used to prepare homoallylic alcohols with trichloro-1,3,5-triazene. Further, it plays an important role for tetrakis(triphenylphosphine)palladium(0) catalyzed coupling reaction with iodoquinones and allyl acetates.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Allyltri-n-butyltin acts as an allylation reagent for aldehydes catalyzed by chiral Lewis acids and ytterbium(III) trifluoromethanesulfonate. It is also used to prepare homoallylic alcohols with trichloro-1,3,5-triazene. Further, it plays an important role for tetrakis(triphenylphosphine)palladium(0) catalyzed coupling reaction with iodoquinones and allyl acetates.

Solubility
Immiscible with water.

Notes
Air sensitive. Incompatible with strong oxidizing agents.

RUO – Research Use Only

General References:

Widely used nucleophilic, non-basic allylating agent.
Couples with primary or secondary alkyl halides under free-radical conditions: J. Am. Chem. Soc., 104, 5829 (1982); Bull. Chem. Soc. Jpn., 56, 24801 (1983).
Lewis acid-catalyzed stereoselective addition to aldehydes gives homoallylic alcohols: Chem. Lett., 919 (1979); Tetrahedron Lett., 25, 265, 1879 (1984); Synlett, 1694 (2002). For chemoselective allylation of aldehydes in the presence of ketones, see: Tetrahedron Lett., 36, 3723 (1995). In the presence of TI(O-i-Pr)₄ and BINOL, enantioselective allylation of ketones can be accomplished with high ee: Tetrahedron: Asym., 11, 4163 (2000).
Similarly, homoallylamines are formed from aldimines with TiCl₄ or BF₃ etherate: J. Org. Chem., 50, 146 (1985). For allylation of quinones, see p-Benzoquinone, A13162.
Lumbroso, A.; Catak, S.; Sulzer-Mossé, S.; Mesmaeker, A. D. Efficient access to functionalized cyclobutanone derivatives using cyclobuteniminium salts as highly reactive Michael acceptors. Tetrahedron Lett. 2015, 56 (19), 2397-2401.
Rajesh, A.; Sharma, G. V. M.; Damera, K. Toward the stereoselective synthesis of C1-C23 fragment of spirastrellolide B. Tetrahedron Lett. 2014, 55 (30), 4067-4070.