Location: Bowdoin / Richard D. Broene

Chemistry

Richard Broene

Professor of Chemistry

Contact Information

rbroene@bowdoin.edu
207-725-3626
Chemistry
50 Druckenmiller Hall



Fall 2014

  • Organic Chemistry I (CHEM 2250B)


Broene: Bowdoin College: Chemistry

Education

  • B.S. Chemistry, Hope College (1985)
  • Ph.D. Organic Chemistry, University of California, Los Angeles (1990)

Rick Broene received his BS in Chemistry from Hope College (Holland MI) in 1985 at which time he was was honored with a Sigma Xi summer research award. While at Hope he worked with Mike Doyle investigating the decomposition mechanism of trioxodinitrate(II) in the presence of metalloproteins. He went on to graduate school at UCLA, where he worked with Francois Diederich on the synthesis and study of molecules with high carbon to hydrogen ratios (graphite-like molecules) specifically, the synthesis of circumanthracene. While there he also helped to design and synthesized the first asymmetric podand to be used for molecular recognition. He received his Ph.D. in in 1990. In a complete change of direction after grad school, he was a postdoctoral fellow at MIT, where he studied organometallic chemistry. While there, he reported the first method for highly enantioselective reduction of unfunctionalized trisubstituted olefins and achieved diastereoselective syntheses of indoles, indolines, and isoquinolines using zirconocene intermediates. In 1998, Professor Broene was a Visiting Staff Member at Los Alamos National Lab in New Mexico. While at LANL, he continued to develop his interest in both homogeneous asymmetric catalysis while investigating the immobilization of catalysts on solid supports. This interest was expanded during the 2004-05 academic year when he was a visiting scholar at UNC Chapel Hill working the the broadly defined area of late transition metal catalyzed polymerization reactions. Research grants from the NSF, PRF, Research Corporation, CUR, Pfizer and DOE have enabled 55 students to work on projects in his labs over the past 17 years.

 

Professor Broene's research interests focus on the use of transition and lanthanide-series metals to accomplish asymmetric organic syntheses, dimerizations as well as the rational, metal-facilitated synthesis of ligands for chiral catalyts.

There are several projects currently underway in his research labs. The first investigates the ability of tethered bis-indenyl ligands to serve as proto-C2 symmetric ligands for lanthanide metals, forming metallocene complexes. The work in this area showed that the two-carbon tether was too short to allow the preferred formation of the racemic form of the complex, favoring instead the meso form. This is in part due to the large ionic radius of these f-electron elements. We use both traditional organic chemistry and zirconocene-mediated reactions for the synthesis of these ligands.

A second area investigates the use of conformationally constrained ligands to provide more favorable orientations for cobalt catalyzed dimerization of alpha olefins.  We have synthesized useful quantities of quinoline substituted Cp* ligands and are investigating if they favor 2,1 insertion over 1,2 insertion reactions.  Additionally we have synthesized phosphabenzene and are exploring its coordination chemistry to Co.

Name, "Title", Duration, Post Grad (Degree Program) Listed by Graduation year.

 55 undergraduate student researchers mentored.

2010-2011
Kaitlin Clifford "Synthesis of a Sterically Hindered Metallocene Catalyst"
Type:  Summer and Ind Study

Katherine Rawden "Ligand Variation for a Cobalt Catalyst to Dimerize Linear alpha-Olefins"
Type:  Summer

Taylor Vozniak "8-Quinolinyl-Cyclopentadiene"
Type:  Summer

2009-10
Alex Carpenter "8-Quinolinyl-Cyclopentadiene:  A Ligand for Cobalt Catalyzed alpha -Olefin Dimerization"
Type:  2 Summers and Honors
Post Grad:  UC San Diego (PhD Program)

James Chen "Cp*Co(ethane)L:  Ligand Variations for Regioselection"
Type:  Ind Study

2008-09
Michael Farthing "Catalyst Optimization for the Synthesis of Poly(silyl ether)s"
Type:  Summer

Oronde Cruger "Ligands for Cobalt Catalysts"
Type:  Summer

2007-08
Michael Ardolino "Cationic Cobalt Catalysis:  Improving upon alpha-olefin dimerization
Type:  Honors

Jonathan Freedman "New Synthesis of Chromones"
Type:  Honors
Post Grad:  Boston University (MD/PhD Program)

David Soohoo
"The Use of a Cobalt (I) Catalyst in the Production of Linear α-olefin Products"
Type:  Honors
Post Grad:  SUNY Stony Brook (MD)

Anh Tran "Polysilylethers via Iridium-catalyzed Dehydrocoupling of Diols with Disilanes"
Type:  Ind Study
Post Grad:  Deloitte and Touche

2006-07
Kristen Brownell “ The Synthesis of Enepolyynes” 
Type:  Honors 
Post Grad:  Stanford Uniiversity (PhD)

Ethan Van Arnam “Improving Selectivity of Linear α-Olefin Dimerization to Linear α-Olefin Products by Cobalt Catalysis: Attempted Synthesis of Phosphabenzene as a Cobalt Ligand”
Type:  Honors   
Post Grad:  Cal Tech – Organic Chemistry(PhD)

2005-06
Evron Legall Two summers, two semester Ind Study

2004-05
John Haines “Synthesis of Ferrocene Based Lanthanide Sulfonamide Catalysts”
Type:  Honors 
Post Grad:  University of Maryland (MD)

Andrew Parsons “Towards the Synthesis of C2-Symmetric Ferrocenyl Bis-N-Heterocyclic Carbene Ligands”
Type:  Honors 
Post Grad:  UNC Chapel Hill- Organic Chemistry (PhD)

Lauren Sarno “The Polymerization of COT and Hexadiene using Schrock’s and Grubbs’ Catalysts”
Type:  Summer (Joint with Christensen)
Post Grad:  St. Georges (MD)

Emma Leonard “Metathesis Route to Bridged Bis(allylindenyl) Lanthanocene Chlorides”
Type:  Summer
Post Grad:  University of Texas (Masters in Architecture)

2003-04

Laura Phillips "Synthesis of Chiral Disulfonamide Ligands via 1,1'-Binaphthyl-2,2'-Diamine"
Type: Ind Study
Post Grad:  Dental School

William Stetler "The Synthesis of C2-symmetric Lanthanide Catalysts Using a Ferrocene Backbone"
Type: Honors
Post Grad:  University of Alabama, Birmingham (MD)

James Wilkins "The Synthesis of Tethered Bis-4, 7-diisopropylindene Ligands for Lanthanide Series Metal Catalysts"
Type: Honors
Post Grad: Oxford (Marshall Scholar, PhD), Harvard (MD)

2002-03
Elizabeth Barney "The Use of Ionic Liquids for Lanthanide Reactions"
Type: Honors (Joint with Christensen)
Post Grad:  Tufts University (DVM)

Mara Grossman "The Use of Ionic Liquids for Lanthanide Reactions"
Type: Ind Study
Post Grad: Georgetown (MD)

Ariele Hanek "Synthesis of Bis(Sulfonamide)Ferrocenyl Ligands for Lanthanide Series Metal Catalysis"
Type: Honors
Post Grad: Cal Tech (PhD)

Elise Meoli "Enantioselective Catalytic Capabilities of a Lanthanide Species"
Type: Honors
Post Grad:  University of Rochester (MD)

Sara Wiltshire "Polyene Metathesis Reaction using Schrock's Catalysts"
Type: Ind Study
Post Grad: UC Davis (MS Forensic Chemistry)

2001-02
Kris Bossee "The Synthesis of Bis-Cyclopentadienyl Ligands for Enantioselective Catalysis"
Type: Honors
Post Grad: U Penn (MD)

Matthew Stanton "Enatioselective Synthesis of Tethered Bis-Indenyl-Metallocene Catalysts"
Type: Honors
Post Grad: Duke (MBA)

2000-2001
Eric Woodbury "The Synthesis of C2 Symmetric Lanthanocene Catalysts through the Zirconium-mediated Coupling of Two Alkynes"
Type: Honors
Post Grad: University of California, Davis, Organic Chemistry (PhD)

Eri Yoshida: "Synthesis of C2-Symmetric ansa Lanthanocenes"
Type: Honors
Post Grad: University of Utah, Organic Chemistry (MS)

1999-2000
Robin Bellanca "Synthesis of Tethered Biscyclopentadienyl Ligands by Zircocene-mediated Coupling of Alkenes and Alkynes Followed by CO Insertion "
Type: Ind Study
Post Grad: Harvard Law School

1997-98
Benjamin Davis "Design and Synthesis of C2-Symmetric Ansa Lanthanocenes"
Type: Honors
Post Grad: UC Irvine, Inorganic Chemistry (PhD 2003)

Jennifer Krumper "Zirconium-mediated Reductive Cyclization of Alkenes in the Total Synthesis of Rosemarinecine"
Type: Honors
Post Grad: UC Berkeley- Organic Chemistry (PhD 2004)
Assistant Professor Idaho State University, Post Doc - UC Irvine, Visiting Professor, Bowdoin College (2009)

Jeffrey Rodhe "Synthesis of a C2-Symmetric Diphenyl Aziridine for Use as a Chiral Auxiliary"
Type: Honors
Post Grad: University of Texas Southwest Medical School (MD)

Jessica Brannon "New Routes to a Cp-based Ligand"
Type: Ind. Study

J. Anthony D'Alessio "Synthesis of a Triendiyne for Titanocene-mediated Cyclization"
Type: Ind. Study
Post Grad: UC Berkeley Graduate School

1996-97
Matthew Weiss "The Total Synthesis of Rosemarinecine"
Type: Honors
Post Grad: Yale University- Organic Chemistry (PhD, 2001), Amgen Inc

Christina Jeffris "Zirconocene-based Cyclization Reactions to Produce Ligands for Lanthanide Complexes"
Type: Ind. Study
Post Grad: University of Washington Medical School (MD)

Michael Kaufmann " Synthesis of Zirconocene Ligands"
Type: Ind. Study
Post Grad: University of Rochester (MD)

Christina Marchetti "A Palladium-catalyzed Route to Decapentaene"
Type: Ind. Study
Post Grad: Johns Hopkins University- Molecular Biophysics (PhD) Post Doc, NIH

1995-96
Benjamin Nolan "Synthesis and Hydrogenation/Cyclic Amination of Imino Olefins by Lanthanocene Complexes"
Type: Honors
Post Grad: Colorado State University- Inorganic Chemistry (PhD, 2000) Veterinary School, Tufts

Michael Miller "Synthesis and Stabilization of Strained Organic Compounds and the Isolation of Elusive Molecules"
Type: Honors
Post Grad: UCLA - Organic Chemistry (PhD, 2000) Post-Doc - Scripps

Scott Sternson "The Synthesis of (-) Rosmarinecine Utilizing a Zirconium-Mediated Ring Closure"
Type: Honors
Post Grad: Harvard University- Organic Chemistry (PhD, 2001) Post Doc, Rockefeller University

Jennifer Krumper "The Synthesis of Decapentaene"
Type: Ind. Study

1994-95
Andrew Gilbert "Synthesis of Chiral C2-Symmetric Ansa-Lanthanocenes"
Type: Honors
Post Grad: University of Maine, Forestry (MS)

Heather Standley "Stabilization of Strained Cyclic Organic Molecules through Zirconocene Complexation"
Type: Ind. Study
Post Grad: University New South Wales, Australia- Biology

Rachael Cleaves "The Production of C2-Symmetric Ligands for use in Lanthanocene Catalysts"
Type: Ind. Study
Post Grad: Veterinary Assistant- Anchorage, Alaska

1993-94
Joanne Holland "Stabilization of Strained Species by Zirconocene Complexation"
Type: Honors
Post Grad: University of Pennsylvania- Organic Chemistry (PhD, 1999), Chemist- Biogen

Susan Millar "The Synthesis of Novel C2-Symmetric Ligands for Lanthanocene Catalyzed Reactions"
Type: Honors
Post Grad: University of Rochester- Inorganic Chemistry (PhD, 1999)