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K. Barry Sharpless named 2019 Priestley Medalist Scripps Research Institute chemist honored for inventing catalytic, asymmetric oxidation methods and pioneering click chemistry bling molecules. Sharpless dubbed the concept click chemistry: rapid, irreversible reactions that “click” two molecules together in high yields, generating only inoffensive by-products that can be removed without chromatography. In recognition of this and his Nobel Prize-winning work, Sharpless will receive the Priestley Medal, the American Chemical Society’s highest honor, in 2019. “The ink had scarcely dried on his Nobel certificate before he introduced the most enduring of his click reactions: the copper-catalyzed version of the reaction of azides and acetylenes,” says Julius Rebek Jr., also a chemist at Scripps Three examples of click reactions used to assemble Research Institute California. “It has had countless applications a vast array of molecules in organic synthesis, medicinal Copper-catalyzed azide-alkyne cycloaddition R chemistry, chemical biology, and 1 materials science. It has been N N used for protein and nucleic N Cu (I) catalyst R1 N+ - + R acid labeling, in vitro and in vivo 2 N N imaging, drug synthesis, and R2 assembly of complex molecular architectures. Even I have used Sulfur(VI) fluoride exchange it.” When other methods failed, O O O O Rebek says, he used click + H2N—R2 chemistry to anchor S S R2 + HF R1 R1 F N uranyl ion cheH lating agents to CH3 CH3 O O O O polymer supR ports for exSi O 2 Si F + S S R2 + R1 R1 tracting the ion F O CH3 CH3 from seawater. R1, R2 = various Phil S. Baran, When K. Barry Sharpless won the Nobel Prize in Chemistry in 2001 for his work on chirally catalyzed oxidation reactions, he wrote in his biographical sketch that much of his childhood’s daydreaming was dedicated to fishing at his family’s cottage on the New Jersey shore. “While I had an overwhelming passion for fishing, school I merely enjoyed and I never planned to be a scientist,” he noted. After garnering a Nobel Prize, many would be tempted to kick back and put out the proverbial “gone fishin’ ” sign. But not Sharpless. Instead, the Scripps Research Institute California chemist dove into a risky line of research that has given chemists of all stripes a remarkably reliable tool for assem-
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C&EN | CEN.ACS.ORG | JUNE 25, 2018
another Scripps chemist, says when he was a graduate student at the school, he observed “how Barry’s colleagues, and indeed the majority of the chemical community, thought he was completely out of his mind when he first started this line of research.” Now, Baran notes, “nearly every paper I see on polymers, chemical biology, materials, and supramolecular chemistry uses his reactions. This is what chemistry should be about—identifying or inventing new reactivity that makes the world a better place.” “Dr. Sharpless has made numerous contributions to chemistry that have each significantly moved the field forward,” says Thomas Connelly, ACS executive director and CEO. “His service to advancing chemistry is beyond measure. He is truly deserving of the Priestley Medal, and I offer my heartfelt congratulations.” Sharpless says at first he didn’t think he deserved the Priestley Medal, but he acknowledges that click chemistry has been extremely useful. “Chemists, we’re all served by a reaction that works,” he says. He also notes that his wife, Jan, came up with the catchy click chemistry descriptor. Sharpless wanted to call it neat chemistry—a reference to whiskey that’s served straight. “I happened to read the biography of professor Sharpless published by the Nobel Foundation, and in it, I discovered a kindred spirit: a love of the sea and fishing—a spirit of seeking,” 2018 ACS President Peter Dorhout adds. “The highest award of recognition from the ACS is one big one that will not get away.”—BETHANY HALFORD
C R E D I T: S C R I P PS R ES EA RC H
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