Home
Resources
Publications
Direct Conversion of Carbonyl Compounds Into Organic Halides: Indium(III) Hydroxide-Catalyzed Deoxygenative Halogenation Using Chlorodimethylsilane

Direct Conversion of Carbonyl Compounds Into Organic Halides: Indium(III) Hydroxide-Catalyzed Deoxygenative Halogenation Using Chlorodimethylsilane

Yoshiyuki Onishi, Daigo Ogawa, Makoto Yasuda, Akio Baba

J Am Chem Soc. 2002 Nov 20;124(46):13690-1.

PMID: 12431095

Abstract:

The reaction of carbonyls and chlorodimethylsilane was effectively catalyzed by indium(III) hydroxide and afforded the corresponding deoxygenative chlorination products, in which the carbonyl carbon accepted two nucleophiles (H and Cl) with releasing oxygen. Only In(OH)3 catalyzed the reaction, and typical Lewis acids such as TiCl4, AlCl3, and BF3.OEt2 showed no catalytic activity. The reaction mechanism of this deoxygenative chlorination includes initial hydrosilylation followed by chlorination. Other nucleophiles such as allyl or iodine were available for this methodology. The moderate Lewis acidity of indium catalyst enabled chemoselective reaction, and therefore ester, nitro, cyano, or halogen groups were not affected during the reaction course.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP20661216	Indium(III) hydroxide		20661-21-6	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: