It was previously reported that the palladium-catalyzed cross-coupling reaction of 1-alkenylboron compounds with various vinylic or aryl halides in the presence of base provides the corresponding coupling products in high yields, stereoand regioselectively. The recent progress of such reactions, including the reaction of sterically hindered arylboronic acids with sterically hindered haloarenes,...

Haloorganic biocides are widely employed as soil fumigants to combat the destructive action of plant parasitic nematodes and fungi. These substances are dehalogenated by soil organisms, principally species of Pseudomonas and Flavobacteria, to nontoxic metabolities. The paths of metabolism of a vareity of simply alkyl halides are described with emphasis upon the biodehalogenation step.

This article is a short overview of some recent research activity in the Laboratory of Inorganic Synthesis and Catalysis (LSCI) at EPFL-ISIC. It summarizes the work on Ni-catalyzed cross-coupling reactions of non-activated alkyl halides. It then describes and discusses the work on the bio-mimetic chemistry of [Fe]-hydrogenase.

α-Halocarbonyl compounds undergo β-hydrogen elimination to give conjugated olefins in the presence of a transition-metal catalyst. However, a copper/triamine catalyst system can induce the alkylative Mizoroki–Heck reaction of styrenes with tertiary-alkyl halides possessing a withdrawing group under very mild conditions. This reaction provides an efficient synthetic methodology for tertiary-alky...

[equation: see text] An efficient one-pot route to unsymmetrical diorganyl selenides has been developed by ruthenium(III) chloride catalyzed reactions of dibenzyl or diphenyl diselenides with alkyl halides in the presence of zinc. Organic iodides, bromides, and activated chlorides underwent the reactions efficiently. Unreactive organic chlorides also underwent the same type of selenation with s...

The addition of Grignard reagents or organolithium reagents to the SO2-surrogate DABSO generates a diverse set of metal sulfinates, suitable for direct conversion to sulfone products. The metal sulfinates can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums.

In this article, we report on the direct Csp-Csp crosscoupling of diarylzinc reagents with benzylic, 1°, 2° and 3° alkyl halides. Under etherate-free conditions, cross-coupling proceeds rapidly at ambient temperature with benzylic, 2° and 3° alkyl halide substrates without addition of an external catalyst. The Csp-Csp cross-coupling has excellent functional group tolerance and products are isol...

Although enantioconvergent alkyl-alkyl couplings of racemic electrophiles have been developed, there have been no reports of the corresponding reactions of racemic nucleophiles. Herein we describe Negishi cross-couplings of racemic α-zincated N-Boc-pyrrolidine with unactivated secondary halides, thus providing a one-pot, catalytic asymmetric method for the synthesis of a range of 2-alkylpyrroli...

While previous studies have identified FeMes2(SciOPP) as the active catalyst species in iron-SciOPP catalyzed Kumada cross-coupling of mesitylmagnesium bromide and primary alkyl halides, the active catalyst species in cross-couplings with phenyl nucleophiles, where low valent iron species might be prevalent due to accessible reductive elimination pathways, remains undefined. In the present stud...

Alkylmalonic esters, which have been recognized as important intermediates in the syntheses of various carboxylic acids, amino acids, etc., can be obtained by a variety of methods.1) Excepting the introduction of tertiary alkyl groups, the alkylation of malonic esters with alkyl halides in basic conditions, for example, in ethanol in the presence of sodium ethoxide, is one of the most important...