Robert G. Bergman

was born in Chicago on May 23, 1942. After completing his undergraduate studies in chemistry at Carleton College in 1963, he received his Ph.D. at the University of Wisconsin in 1966 under the direction of J. A. Berson. While at Wisconsin he was awarded a National Institutes of Health (NIH) Predoctoral Fellowship. Bergman spent 1966 and 1967 as a NATO Fellow in R. Breslow’s laboratories at Columbia, and following that went to the California Institute of Technology as a Noyes Research Instructor. He was promoted to assistant professor in 1969, associate professor in 1971, and full professor in 1973. He accepted an appointment as Professor of Chemistry at the University of California, Berkeley, in 1977, where he was appointed Gerald E. K. Branch Distinguished Professor in 2002. During his long scientific career, Bergman has received many awards and honors, which include the ACS Award in Organometallic Chemistry (1986), the Arthur C. Cope Scholar Award (1987), the E. F. Smith Award (1990), the I. Remsen Award (1990), a MERIT Award from the NIH (1991), the E. O. Lawrence Award in Chemistry from the U.S. Department of Energy (1994), the ACS Arthur C. Cope Award (1996), a Guggenheim Fellowship (1999), the American Institute of Chemists Chemical Pioneer Award (1999), the E. Leete Award for Teaching and Research in Organic Chemistry (2001), and a number of visiting professorships. He will soon receive the 2003 ACS James Flack Norris Award in Physical Organic Chemistry. Bergman is a member of the National Academy of Sciences (since 1984) and the American Academy of Arts and Sciences (since 1984) and has served on many academic and administrative committees and review boards. He has been or is currently a member of the Editorial Advisory Boards of several scientific journals (e.g., Journal of Organic Chemistry, Organometallics, Chemical Reviews, International Journal of Chemical Kinetics, Synlett, and Organic Letters).

Scientific Sketch

Research in the Bergman group centers on organic and organometallic reactions that take place in homogeneous solution. Bergman’s early work in physical organic chemistry led to the discovery of the so-called “Bergman cyclization.” In this process, cis-enediynes cyclize when heated to generate 1,4-benzenoid diradicals (Fig. I), which then abstract hydrogen or halogen atoms to give stable aromatic products (Acc. Chem. Res. 1973, 6,25).

Figure I. Thermal cyclization/aromatization of cis-hex-3-ene-1,5-diyne.

In his more recent studies, Bergman has focused on organometallic chemistry and homogeneous catalysis. Bergman’s primary goals are to develop new stoichiometric and catalytic processes and to gain fundamental understanding of their mechanisms. One major effort is directed toward carbon-hydrogen (C-H) bond activation reactions. This involves the development and study of metal complexes that undergo intermolecular oxidative addition with the normally inert C-H bonds in alkanes and other organic molecules.

Figure 2. Ring-closure reactions catalyzed by Rh(I) that employ a C-H-activation step.

This process holds potential for converting methane and other hydrocarbons into useful functionalized organic molecules. Recent efforts have yielded directed catalytic C-H activation reactions that lead to efficient cyclization of a variety of organic substrates (Fig. 2, J. Am. Chem. Soc. 2001, 123, 2685).

A second major area of investigation involves the study of the mechanisms of metal-mediated atom- and group-transfer processes using organometallic complexes having metal-oxygen, -nitrogen, and -sulfur bonds. Recent efforts in this area have yielded early transition metal imido (M=NR) complexes that undergo highly enantioselective cycloaddition reactions between metal-nitrogen multiple bonds and substituted allenes, (Fig. 3, Angew. Chem. Int. Ed. 2000, 39, 2339) and the discovery of complexes with exceptionally basic nitrogen ligands.

Figure 3. The use of enantioresolved imido complexes in the kinetic resolution of chiral allenes.

These reactions are being applied to the development of efficient catalytic carbon-nitrogen bond-forming processes such as carbon-carbon multiple bond hydroamination reactions. Other projects in the group are directed at the design and synthesis of novel ligands for transition metal centers, and heterobinuclear complexes, that should provide entries to new and more selective catalytic transformations. Density functional theory is being used to supplement understanding obtained from mechanistic experiments and to help determine the direction of new experimental work.

Potato Latkes (Potato Pancakes): A Traditional Jewish Chanukah Dish

Starting materials:

6 large potatoes

1 small onion

2 eggs

3 tbsp flour

¼ tsp pepper

1 tsp salt

1 tsp baking soda

Peel the potatoes and store them in a bowl of cold water to keep them from oxidizing. Grate the potatoes and onion as quickly as possible. Separate the liquid. Add the other ingredients and mix well. The consistency should be somewhat thick; add more flour if it seems too runny. Pour 60 mL oil into heated frying pan. When the oil bubbles, spoon pancake-sized portions onto a hot, pre-greased skillet. Turn when golden brown. Be sure to add fresh oil as needed so the potatoes do not burn. When both sides are golden brown, remove the latkes with a slotted spatula so that the oil will drain off, and layer on a plate between paper towels, which will absorb more oil. Continue until all of the potato batter is used. Serve hot with applesauce or sour cream.

«In the second century B.C., the inhabitants of Judea joined a rebellion against the kingdom of Antiochus IV under the leadership of a country priest named Mattathais and his five sons (of whom Judah became the most famous, known as “the hammer” or Maccabee). The Maccabees and their followers used guerrilla tactics to win the first national liberation struggle in recorded history. In 165 B.C. they retook Jerusalem, purified and rededicated the Temple, which had been vandalized and desecrated, and rekindled the eternal light, which is always to be kept burning. They had only a small amount of oil, but the holiday of Chanukah (which means “dedication”) was established to commemorate the legend that this small amount of oil kept the eternal light burning for eight days.

Potato latkes (potato pancakes) are a dish that Jews traditionally serve during the Chanukah holiday. It is certainly not clear that potatoes were available in ancient times, so the dish was probably developed in eastern Europe. The latkes are cooked in oil, another means of commemorating the eternal light legend.»

Robert G. Bergman