DR.

GHAYOOR ABBAS CHOTANA

GHAYOOR786@HOTMAIL.COM +092 (042) 772-5451 CEL:0333-444 0554

DEPARTMENT OF CHEMISTRY AMIN PARK, RAVI ROAD LAHORE 54000, PAKISTAN NIC # 35202-2252850-1

INORGANIC/ORGANOMETALLIC SCIENTIST WITH EXPERTISE IN HOMOGENOUS CATALYSIS AND ORGANIC SYNTHETIC METHODOLOGY

PERSONAL DATA
Nationality
Pakistani

Date
Lahore Feb 09, 1976

and ID

Place

of Card

Birth # Address

National
35202-2252850-1

Home
Lahore Feb 09, 1976

Telephone
Lahore Feb 09, 1976

Date
Lahore Feb 09, 1976

and

Place

of

Birth

Ph.D. Chemistry (Organometallic)

Jan 2002 Jan 2008 Michigan State University, East Lansing, Michigan USA. Advisor: Milton R. Smith III Thesis Title: Iridium Catalyzed Aromatic Borylation and its Applications in One-Pot Preparations of Substituted Aromatic Building Blocks

EDUCATION
Post Doctoral Associate
March 2008 March 2009 Indiana University, Bloomington, USA. Advisor: Dan J. Mindiola

Ph.D. Chemistry (Organometallic)

Jan 2002 Jan 2008 Michigan State University, East Lansing, Michigan USA. Advisor: Milton R. Smith III Thesis Title: Iridium Catalyzed Aromatic Borylation and its Applications in One-Pot Preparations of Substituted Aromatic Building Blocks

M.Sc. Chemistry (Inorganic/Analytical)

Feb 1996 Feb 1998

Quaid-i-Azam University, Islamabad, Pakistan. Advisor: M. Ikram Thesis Title: Levels of Selected Toxic Metals in Solvent Based Paints Manufactured in Pakistan

B.Sc.
August 1993 August 1995 Govt. College University, Lahore, Pakistan. Majors: Chemistry, Statistics, Zoology

AWARDS
US Presidential Green Chemistry Challenge Award 2008
For Developing Green Technology for the Preparation of Aryl Boronic Esters.

FELLOWSHIPS, HONORS & AWARDS

Invited Speaker in the Prestigious Gordon Graduate Organometallic Seminar, July 6-8, 2007, Salve Regina University, Newport, USA. Dissertation Completion Fellowship, 2007, Michigan State University, East Lansing, USA. Carl H. Brubaker Endowed Fellowship, summer 2004, Michigan State University, East Lansing, USA. Certificate of Merit and Chancellors Gold Medal for 1st position in M.Sc. Chemistry, Session 1996 1998, Quaid-i-Azam University, Islamabad, Pakistan. Graduate Research Assistantship/Scholarship, Michigan State University, USA. 2002-2007. Secured 850/890 (84 Percentile) in GRE International Subject Test. Was awarded PhD Scholarship for securing highest GRE Subject Test Score from Pakistan by Higher Education Commission, Govt. of Pakistan however that Scholarship was not availed.

RESEARCH EXPERIENCE Postdoctoral Research Associate

2008 March 2009 March

Department of Chemistry, Indiana University, Bloomington, USA

Worked on titanium catalyzed carboamination of alkynes with a- unsaturated aldimines.

Graduate Research Assistant

Jan 2002 - Jan 2008

Department of Chemistry, Michigan State University, USA.

Synthesized, isolated and characterized the first examples of 16-electron Iridium tris-boryl complexes, which are the proposed active catalysts/intermediates in catalytic aromatic borylation reactions. Synthesized a variety of novel heteroaromatic boronate esters (of thiophenes, furans, pyrroles, indoles, azaindoles, imidazoles, pyridines, as well as of simple aromatics) by Iridium catalyzed C-H activation/borylation, which are highly valuable synthetic intermediates. Demonstrated that the principle of Sterically Directed Regioselectivity is feasible in

1,4-di-substituted aromatics (i.e. beyond the typical 1,3-di-substituted cases). Thus various ortho borylated benzonitriles were synthesized by regioselective Iridium catalyzed aromatic C-H activation/borylation of 4-substituted benzonitriles. Worked out catalyst design & ligand modifications for improved regioselectivities in aromatic C-H activation/borylation. Scaled up Iridium catalyzed aromatic/heteroaromatic borylation reactions. Developed several One-pot borylation/cross coupling methodologies (i.e. BuchwaldHartwig amination, Sonogashira coupling, C-S and C-O coupling) to synthesize boronate esters of aromatic amines, alkynes, and thio ethers.

Research Assistant
February 1998

February 1997 -

Central Laboratory for Environmental Analysis, Federal Environmental Protection Agency, Pakistan
Analyzed solvent-based paints manufactured in Pakistan for levels of selected toxic metals (Lead, Chromium, Copper, Iron, Zinc) by Flame Atomic Absorption Spectroscopy.

TEACHING EXPERIENCE Visiting Assistant Professor

July 2009 to date

Department of Chemistry, LUMS SSE, Lahore Pakistan.

Teaching introductory organic chemistry to freshman students. Teaching sophomore organic chemistry lab.

Graduate Teaching Assistant

2002 Jan 2007

Jan

Department of Chemistry, Michigan State University, USA.

Teaching assistant for graduate organometallic chemistry course. Preparing home work assignments and grading. Teaching assistant for undergraduate inorganic chemistry laboratory (seniors), and general chemistry laboratory (freshman) courses.

Lecture in Chemistry
Govt. College University Lahore, Pakistan.
1999 - Dec 2001 1999 - Dec 1999 Dec Jan

Department of Education, Govt. of Punjab, Pakistan. Chinar Army Public School and College Murree, Pakistan.
Mar 1998 - Jan 1999 Teaching inorganic chemistry (M.Sc) and physical chemistry (B.Sc) courses. Curriculum development of various inorganic chemistry (M.Sc) courses. Teaching general chemistry (F.Sc) theory and laboratory practicals.

COURSE WORK Graduate courses

Advanced Inorganic Chemistry I (Chemical Applications of Group Theory) Advanced Inorganic Chemistry II (Fundamental Concepts and Descriptive Inorganic Chemistry)

Selected Topics in Inorganic Chemistry (Crystallography) Organometallic Chemistry Structure & Spectroscopy of Organic Compounds Methods of Organic Synthesis

Undergraduate courses
Coordination Chemistry Chemistry in Non-Aqueous Solvents Symmetry and Group Theory Industrial Chemistry Organometallic Chemistry Instrumental Analysis Nuclear & Radio Chemistry Advanced Analytical Chemistry

PUBLICATIONS JOURNAL PUBLICATIONS

Chotana, Ghayoor A.; Kallepalli, V. A.; Maleczka, R. E., Jr.; Smith, M. R., III. Iridium catalyzed Borylation of Thiophenes: Versatile, Synthetic Elaboration Founded on Selective CH Functionalization Tetrahedron 2008, 64 (26), 6103-6114. Invited paper in the special issue of Tetrahedron on Catalytic Aromatic CH Activation. Paul, S.; Chotana, Ghayoor A.; Holmes, D,; Reichle, R. C.; Maleczka, R. E., Jr.; and Smith M, R. III. Ir Catalyzed Functionalization of 2-Substituted Indoles at the 7-Position: Nitrogen Directed Aromatic Borylation J. Am. Chem. Soc. 2006, 128 (49), 15552-15553. Holmes, D.; Chotana, Ghayoor A.; Maleczka, R. E., Jr.; Smith, M. R., III. One-Pot Borylation/Amination Reactions: Synthesis of Arylamine Boronate Esters from Halogenated Arenes Org. Lett. 2006, 8 (7), 14071410. Chotana, Ghayoor A.; Rak, M. A.; Smith, M. R., III. Sterically directed Functionalization of Aromatic C-H bonds: Selective Borylation ortho to Cyano Groups in Arenes and Heterocycles J. Am. Chem. Soc. 2005, 127 (30), 10539-10544. Ikram, M.; Rauf, M.; Chotana, Ghayoor A.; Bukhari, N. Levels of Lead in Solvent & Water Based Paints Manufactured in Pakistan Sci. Int. (Lahore, Pakistan), 2000, 12 (3), 255-256. Chotana, Ghayoor A.; Maleczka, R. E., Jr.; Smith, Milton R. III. Bis-oxazoline Ligands for Improved Regioselectivities in Iridium Catalyzed Aromatic/Heteroaromatic Borylation (To be submitted in Angew. Chem., Int. Ed. Engl.). (In Process) Chotana, Ghayoor A.; Maleczka, R. E., Jr.; Smith, Milton R. III. One-Pot BorylationSonogashira Coupling Reactions: Synthesis of Aromatic Alkynyl Boronate Esters (To be submitted in Org. Lett.). (In Process) Chotana, Ghayoor A.; Maleczka, R. E., Jr.; Smith, Milton R. III. One-Pot Borylation- CS Coupling Reactions: Synthesis of Aromatic Thioether Boronate Esters (To be submitted in Tetrahedron Lett.). (In Process) Chotana, Ghayoor A.; Maleczka, R. E., Jr.; Smith, Milton R. III. Steric Effects of Phosphine Ligands on Structure and Reactivity of Iridium Tris-Boryl Complexes (To be submitted in J. Am. Chem. Soc.). (In Process) Chotana, Ghayoor A.; Wicker, B. F.; Aneetha, H.; Basuli, F.; Mindiola, D. J.; Titanium Catalyzed Carboamination of Alkynes (To be submitted in Organometallics). (In Process)

Patents:
Smith, M. R., III.; Maleczka, R. E., Jr.; Chotana, Ghayoor A.; Kallepalli, V. A.; Paul, S. Process for the Preparation of Borylated Thiophenes. U.S. Pat. Appl. Publ. 20080091035, 2008. Smith, M. R., III.; Maleczka, R. E., Jr.; Chotana, Ghayoor A.; Paul, S. Process for the Preparation of 2-Substituted-7-Boryl Indoles and Compounds. U.S. Pat. Appl. Publ. 20080167476, 2008. Smith, M. R., III.; Maleczka, R. E., Jr.; Chotana, Ghayoor A. Catalytic ortho Borylation of Substituted Benzonitriles and Cyano Substituted Heteroaromatics. U.S. Pat. Appl. Publ. 20060281939, 2006, and WO/2006/135705. Smith, M. R., III.; Maleczka, R. E., Jr.; Chotana, Ghayoor A.; Paul, S.; Kallepalli, V. A. Iridium-Catalyzed C-H Borylation/Deborylation for the Syntheses of Unique Boronate Esters. U.S. Pat. Appl. 2007. (In Process) Smith, M. R., III.; Maleczka, R. E., Jr.; Chotana, Ghayoor A. Five-coordinate, Constrained Geometry Catalysts for Iridium catalyzed C-H Borylation. U.S. Pat. Appl. 2007. (In Process)

INVITED TALKS:
Chotana, Ghayoor A.; Steric Effects of Phosphine Ligands on Structure and Reactivity of Iridium Tris-boryl Complexes. Invited talk in the 1st Gordon Graduate Organometallic Chemistry Seminar, July 6-8, 2007, Salve Regina University, Newport, USA. Chotana, Ghayoor A.; Synthetic Applications of Iridium Catalyzed Aromatic Borylation. Invited talk in the Organometallic Chemistry Seminar Series at University of Michigan Ann Arbor, February 2005.

Conference Publications/Oral Presentations:

Chotana, Ghayoor A.; Iridium Catalyzed Aromatic C-H Activation/Borylation. First Chemistry Alumni Meeting and Seminar on Frontiers of Chemistry May 15-16, 2009, Department of Chemistry, Quaid-i-Azam University, Islamabad Pakistan. Vanchura, B. A.; Ramanathan, B-S.; Chotana, Ghayoor A.; Smith, Milton R. III. Iridium Catalyzed Aromatic Borylation: Whats up with the Metal? Abstracts of Papers, 237th ACS National Meeting, Salt Lake City, UT, United States, March 22-26, 2009. Maleczka, R. E., Jr.; Cho, J-Y.; Chotana, Ghayoor A.; Holmes, D.; Iverson, C. N.; Kallepalli, Venkata A.; Norberg, M.; Onyeozili, E. N.; Paul, S; Sanchez, L.; Shi, F.; Tse, M-K.; Smith, Milton R. III. Green Chemistry for Preparing Boronic Esters. Presidential Green Chemistry Challenge Award Section of the 12th Annual Green Chemistry and Engineering Conference, Washington, DC, June 24-26, 2008. Maleczka, R. E., Jr.; Chotana, Ghayoor A.; Kallepalli, V. A.; Holmes, D.; Norberg, M.; Sanchez, L.; Shi, F.; Smith, Milton R. III. Catalytic Borylation/Cross-Coupling Protocols that avoid the Preparation of Haloaromatics. Abstracts, 40th Middle Atlantic Regional Meeting of the American Chemical Society, Queens, NY, United States, May 17-21, 2008. Chotana, Ghayoor A.; Vanchura, B. A.; Smith, Milton R. III. Syntheses of Five-coordinate Intermediates in Ir-catalyzed Borylations. Abstracts of Papers, 234rd ACS National Meeting, Boston, MA, United States, August 19-23, 2007. Chotana, Ghayoor A.; Maleczka, R. E., Jr.; Smith, Milton R. III. Syntheses and Catalytic Activity of Tris-Boryl Iridium Complexes. Abstracts of Papers, 233rd ACS National Meeting, Chicago, IL, United States, March 25-29, 2007. Chotana, Ghayoor A.; Paul, Sulagna; Kallepalli, Venkata A.; Maleczka, R. E., Jr.; Smith, Milton R. III. Ir-catalyzed Borylation: Functionalization of C-H bonds in Heterocycles. Abstracts of Papers, 232nd ACS National Meeting, San Francisco, CA, United States, Sept. 10-14, 2006. Chotana, Ghayoor A.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Tandem Aro-

matic C-H activation/Borylation C X coupling. Abstracts of Papers, 230th ACS National Meeting, Washington, DC, United States, Aug. 28 Sept.1, 2005. Paul, S; Holmes, D.; Chotana, Ghayoor A.; Smith, Milton R. III. Regioselective C-H Activation of Indoles. Abstracts of Papers, 230th ACS National Meeting, Washington, DC, United States, Aug. 28-Sept. 1, 2005, Kallepalli, V. A.; Chotana, Ghayoor A.; Maleczka, R. E., Jr.; Smith, M. R., III. Regioselective Borylation of Pyrroles and Azaindoles. Abstracts of Papers, 230th ACS National Meeting, Washington, DC, United States, Aug. 28-Sept.1, 2005.. Chotana, Ghayoor A.; Rak, M. A.; Smith, M. R., III. Sterically Directed Functionalization of Aromatic C-H bonds: Selective Borylation ortho to Cyano Groups in Arenes and Heterocycles. 39th National Organic Chemistry Symposium, University of Utah, June 12-16, 2005. Shi, F.; Holmes, D.; Chotana, Ghayoor A.; Gong, Y.; Smith, M. R., III; Maleczka, R. E., Jr. C H Activation/Borylation-based One-pot Preparations of Substituted Aromatic Building Blocks for Organic Synthesis. Abstracts, 36th Central Regional Meeting of the American Chemical Society, Indianapolis, IN, United States, June 2-4, 2004.

SKILL SET
Teaching undergraduate and graduate level chemistry courses. Independent in designing new research projects, and, guiding undergraduate students in research. Proficient in handling air/moisture sensitive materials and Dry box maintenance. Inorganic/Organometallic catalysis, aromatic C-H activation/borylation with interesting and unique regioselectivities. Experienced in ways to design and improve catalysts to shift regioselectivities. Synthesis, isolation and characterization of early and late transition metal complexes. Synthesis, purification, & full characterization of small organic molecules. Synthetic Methodologies: Aromatic/heteroaromatic boronate ester synthesis, well experienced in a variety of organic coupling chemistry (Suzuki, Sonagashira, Buchwald/Hartwig Amination, C-S). Purification Techniques: Column chromatography, TLC, Vacuum and reduced pressure distillations, Crystallization. Structure elucidation & regiochemical assignments by 2D NMR, Heteronuclear (31P, 11B, 19F) NMR. Scale up of reactions from mg to 100s of grams for BoroPharm, Inc. Instrumentation: Routine maintenance of GC-MS including trap cleanup, Tuning NMR for various nuclei, FT-IR, Atomic Absorption Spectroscopy. Chemistry Software (ChemOffice) & Search engines (SciFinder Scholar, Beilstein, Web of Science), EndNote. Statistical Analysis.

AFFILIATIONS:
American Chemical Society, Division of Inorganic Chemistry and Organic Chemistry.

Co Curricular Activities:
Member, Quaidian Blood Donors Society, Quaid-i-Azam University Islamabad, Pakistan, 1996-1998. Executive Member, Environmental Protection Society, Government College Lahore,

Pakistan, 1993-1995. Member, Horticultural Society, Government College Lahore, Pakistan, 1993-1995.

Management Experience:
Presiding Officer, Old Ravian Union Election, April 30, 2000. Presiding Officer, Local Bodies Election, May 20, 1998. Assistant House Parent Khyber house, Chinar Army Public School and College Murree, Pakistan, Oct 1998-Jan 1999. M.Sc. Class Representative, Chemistry Dept., Quaid-i-Azam University Islamabad, Jan 1997-Jan 1998. Arranging Welcome and Farewell parties, Study trips/tours, Fun fare etc.

REFERENCES:
Milton R. Smith III (PhD Advisor) Dept. of Chemistry, Michigan State University, USA 517-355-9715 X 166. smithmil@msu.edu Robert E. Maleczka, Jr. (Co author on papers from PhD work, and was present in all PhD research group meetings) Dept. of Chemistry, Michigan State University, USA 517-355-9715 X 124. maleczka@chemistry.msu.edu M. Mazhar, Dept. of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan. 09251-90642106. mazhar42pk@yahoo.com M. Saqib Ali, Dept. of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan. 09251-90642130. drsa54@yahoo.com James K. McCusker (PhD Committee Second Reader) Dept. of Chemistry, Michigan State University, USA 517-355-9715 X 106. jkm@chemistry.msu.edu