Organic Letters 2010-04-02

Copper-catalyzed diacetoxylation of olefins using PhI(OAc)2 as oxidant.

Jayasree Seayad, Abdul Majeed Seayad, Christina L L Chai

Index: Org. Lett. 12(7) , 1412-5, (2010)

Full Text: HTML

Abstract

Copper(I) or -(II) salts with weakly coordinating anions catalyze the diacetoxylation of olefins efficiently in the presence of PhI(OAc)(2) as the oxidant under mild conditions. The reaction is effective for aryl, aryl alkyl, as well as aliphatic terminal and internal olefins forming the corresponding vicinal diacetoxy compounds in 70-85% yields and dr (syn/anti) of up to 5.2. Under these conditions, homoallylic alcohols formed the corresponding tetrahydrofuran derivatives in high yields.

Related Compounds

  • (Diacetoxyiodo)ben...

Related Articles:

An expedient procedure for the oxidative cleavage of olefinic bonds with PhI(OAc)2, NMO, and catalytic OsO4.

2010-04-02

[Org. Lett. 12(7) , 1552-5, (2010)]

Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds.

2004-08-11

[J. Am. Chem. Soc. 126 , 9542-9543, (2004)]

Determination of vitamin C in tablets and fruits by titration with phenyliodosoacetate.

1982-01-01

[Il Farmaco 37(1) , 9-14, (1982)]

Synthesis of benzimidazoles by PIDA-promoted direct C(sp2)-H imidation of N-arylamidines.

2012-10-29

[Chemistry 18(44) , 13964-7, (2012)]

Structural studies on bioactive compounds. 32. Oxidation of tyrphostin protein tyrosine kinase inhibitors with hypervalent iodine reagents.

2000-04-20

[J. Med. Chem. 43(8) , 1550-62, (2000)]

More Articles...