PALLADIUM-CATALYZED ALKYL-ALKYL SUZUKI CROSS-COUPLINGS OF PRIMARY ALKYL BROMIDES AT ROOM-TEMPERATURE: (13-CHLOROTRIDECYLOXY)TRIETHYLSILANE [Silane, [(13-chlorotridecyl)oxy]triethyl-].

Alkyl-alkyl Suzuki cross-coupling of unactivated secondary alkyl chlorides.

The first method for achieving alkyl–alkyl Suzuki reactions of unactivated secondary alkyl chlorides has been developed. Carbon–carbon bond formation occurs under mild conditions (at room temperature) with the aid of commercially available catalyst components. This method has proved to be versatile: without modification, it can be applied to Suzuki reactions of secondary and primary alkyl bromi...

The First Method for Achieving Palladium-Catalyzed Cross- Couplings of Simple Alkyl Chlorides: Suzuki Reactions Catalyzed by Pd2(dba)3/PCy3

Mild and phosphine-free iron-catalyzed cross-coupling of nonactivated secondary alkyl halides with alkynyl Grignard reagents.

A simple protocol for iron-catalyzed cross-coupling of nonactivated secondary alkyl bromides and iodides with alkynyl Grignard reagents at room temperature has been developed. A wide range of secondary alkyl halides and terminal alkynes are tolerated to afford the substituted alkynes in good yields. A slight modification of the reaction protocol also allows for cross-coupling with a variety of ...

A mild, palladium-catalyzed method for the dehydrohalogenation of alkyl bromides: synthetic and mechanistic studies.

We have exploited a typically undesired elementary step in cross-coupling reactions, β-hydride elimination, to accomplish palladium-catalyzed dehydrohalogenations of alkyl bromides to form terminal olefins. We have applied this method, which proceeds in excellent yield at room temperature in the presence of a variety of functional groups, to a formal total synthesis of (R)-mevalonolactone. Our ...

B-alkyl Suzuki couplings for the stereoselective synthesis of substituted pyrans.

Unprotected homoallylic alcohols can be directly converted to cis-2,6-disubstituted pyrans by palladium catalyzed B-alkyl Suzuki coupling and subsequent Michael addition.