NEWS OF TH E WEEK
COOL FORECAST FOR AG EARNINGS AGRICULTURE: Weak sales to farmers in North America prompt DuPont, FMC to cut estimates UPONT AND FMC have lowered their earnings
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estimates for 2014 because of lower-than-expected agriculture sales in North America in the second quarter. A long, cool spring slowed purchases of crop protection chemicals from both firms. And a shift by farmers from corn to soybeans as a result of low corn prices left DuPont struggling to sell seeds. As a result, DuPont expects earnings of $4.00–$4.10 per share in 2014, compared with a previous estimate of $4.20–$4.45. The company wasn’t prepared for the planting shift because it has not yet introduced its next generation of soybean seeds. “While 2014 is a transition year in agriculture, the revisions to the outlook we made today do not meet the expectations we set for our agriculture segment or for the company,” DuPont CEO Ellen J. Kullman acknowledged. DUPON T
A farmer loads DuPont’s Pioneer Hi-Bred corn seed into his planter.
ALKYLATION ADVANCE ORGANIC SYNTHESIS: Bifunctional catalyst couples ketones with olefins
ATCHMAKING BETWEEN KETONES and
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olefins has never been easy. Although ketones readily pair up with many reagents, thanks to their ability to deprotonate and form nucleophilic enolates, olefins typically rebuff advances from such nucleophilic suitors. Now, O O chemists at the UniversiBifunctional ty of Texas, Austin, have catalyst found a catalyst capable + of forging a carbon-carbon bond between this unlikely pair. A bifunctional “Ketones are very common compounds. Olefins are catalyst weds even more common—they’re readily available feedketones to olefins in stocks,” says Guangbin Dong, the chemistry professor a by-product-free who spearheaded the work. “We thought if we could strategy. find a good way to couple these two together, it would be very useful.” Dong and postdoc Fanyang Mo determined that the ideal matchmaker would be a bifunctional catalyst CEN.ACS.ORG
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At FMC, cold weather that lasted beyond the end of April chilled sales of crop protection products in the second quarter. Under normal weather conditions, for example, farmers would purchase products such as FMC’s Capture LFR corn insecticide, which is applied before seeds germinate. FMC has adjusted its full-year earnings estimate to $4.10–$4.30 per share, down from $4.35–$4.55. Not all agriculture businesses are suffering, however. Monsanto’s most recent earnings report, which was released on June 25, exceeded analysts’ expectations. The seed giant beat DuPont to market with a second generation of yield-improving Roundup Ready soybeans, according to John Roberts, specialty chemical analyst at investment bank UBS. Although the magnitude of DuPont’s problems was larger than expected, the effect on earnings should be temporary and in the longer term be offset by new cost savings, Roberts explained in a note to investors. Those savings will come after DuPont spins off its performance chemicals division into a separate company. Kullman said DuPont will reduce costs by $1 billion or more by the end of 2019 from its 2013 baseline. FMC also plans to split in two by spinning off its alkali chemicals and lithium businesses in early 2015. Once the spin-offs at DuPont and FMC are complete, both companies will be dominated by agriculture and health and nutrition businesses.—MELODY BOMGARDNER
that contains both a secondary amine, 7-azaindoline, and a low-valent rhodium complex (Science 2014, DOI: 10.1126/science.1254465). The amine part of the catalyst activates the ketone by forming an enamine, which is amenable to oxidative addition by the rhodium part of the catalyst. The resulting rhodium hydride coordinates with the olefin, followed by migratory insertion and reductive elimination to generate an alkylated enamine. Hydrolysis produces an α-alkylated ketone and regenerates the catalyst. Dong notes that the reaction has several advantages over traditional ketone alkylations, which typically are done by deprotonating the α-carbon of a ketone and using the resulting enolate to attack an alkyl halide. For example, he says, the new reaction tolerates a broad range of functional groups and is regioselective for alkylating the less hindered side of the ketone. “This is a very cool piece of chemistry,” comments David W. C. MacMillan, an organic synthesis expert at Princeton University. “The capacity to use simple olefins as alkylating reagents for carbonyls is a transformation that is appreciated by the community to be valuable. Although a number of other groups have successfully demonstrated the use of olefins to perform the equivalent of enolate alkylation, this new variant is unique and could find broad application.” Dong hopes to optimize the catalyst so that he might replace rhodium with a less expensive transition metal.—BETHANY HALFORD
JULY 7, 2014
