Dr. Shaukat Ali
Ph.D , China (2012) in Organic Chemistry
Research Interest: Electrophile-driven reactions; C-H bond activation; Triflouromethylation reactions; Asymmetric synthesis; Transition metal-catalyzed cascade reactions
Telephone: +92919216652
Resume: [ Download ]
EDUCATION:
PhD (2012): Organic Synthesis (Group of Prof. Dr. Liang Yong-Min), State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University,China.
MSc Chemistry (2002): Organic Chemistry, Department of Chemistry, Gomal University D. I. Khan, Pakistan
BSc (2000): Chemistry, Department of Chemistry, Government Post Graduate College Mardan, Pakistan
PROFESSIONAL EXPERIENCE:
Present Job Assistant Prof. (Organic Chemistry), Institute of Chemical Sciences, University of Peshawar, Pakistan
2014- 2015 Assistant Professor (Organic Chemistry), Abdul Wali Khan University Mardan, Pakistan
2012- 2014 Assistant Prof. (Organic Chemistry), Islamia College Peshawar, Pakistan
2002-2008 Lecturer in Chemistry, Islamia College University Peshawar (ICUP), Pakistan
2006-2008 Resident Warden, Islamia College University Peshawar (ICUP), Pakistan
SUMMARY OF THE PhD RESEARCH WORK
My Ph.D research mainly consist of two parts:
(a) Electrophile-induced intramolecular amination reactions and cross-amination reactions using molecular iodine (I2) as the electrophilic source and seeking more practical and synthetically useful processes for the synthesis of functionalized quinolines and indolo(2,3-b)quinolines. Highly substituted 3-iodoquinolines bearing different alkyl and aryl moieties were synthesized in moderate to excellent yields (up to 99%) by 6-endo-dig iodocyclization of 2-tosylaminophenylprop-1-yn-3-ols with molecular iodine (I2) under mild conditions. The cyclization was found to be highly regioselective in contrast to the previously repoted Flynn’s approach. The resulting 3-iodoquinolines contain a synthetically useful iodo moiety at position-3 of quinoline nucleus and hence provides an opportunity for further functionalization by various organo-palladium coupling reactions.
In addition, activation of C2 and C3 centers of indoles by molecular iodine (I2) and base followed by in situ reaction with 1-(2-tosylaminophenyl)ketones or 2-tosylaminobenzaldehyde afforded highly substituted indolo(2,3-b)quinolines in moderate to excellent yields (up to 99%). The reaction provides a metal-free selective difunctionalization of indoles. Our simple approach to indolo(2,3-b)quinolines complements existing routes and allows access to some novel C-11-substituted derivatives. The synthetic potential of the protocol was illustrated by the synthesis of neocryptolepine and 11-methylneocryptolepine natural produts. Besides this our group was able to synthesize some other heterocycles and carbocycles.
(b) Transition-metal catalysed cascade reactions and Bronsted-acid catalysis were investigated to disclose some useful methodologies for the synthesis and/or functionalization of medicinally important organic compounds e.g, we were able to discover a method for generating quaternary carbon centers in a single step via palladium catalysis. C-H bond activation via palladium catalysis was also investigated for some reactions, though the results are not convincing to be published.
RESEARCH GRANTS
Award of Startup Research Grant of PKR 0.5 million to Assistant Professors joining under IPFP in 2013, Project Title: Synthesis of functionalized 3-Iodo-1, 2-dihydroquinolines and 5-iodo-10-phenylindeno [2, 1-a]indenes via electrophilic cyclization.
Host Institution: Islamia College University, Peshawar, KPK
Project Duration: 08 months (max.)
RESEARCH STATISTICS/LIST OF PUBLICATIONS:
Total Impact Factor (2014): 114.822
Total Citations up till now: 398 (Google Scholar)
h-index: 10
i-10 index: 11
HEC Approved Supervisor
No. of students M.Phil students under suprvision = 04
No. of students Ph.D students under suprvision = 01
LIST OF PUBLICATIONS:
1. Shaukat Ali, Ying-Xiu Li, Saeed Anwar, Fang Yang, Zi-Sheng Chen, and Yong-Min Liang “One-Pot Access to Indolo[2,3-b]quinolines by Electrophile-Triggered Cross-Amination/Friedel-Crafts Alkylation of Indoles with 1-(2-Tosylaminophenyl) ketones” J. Org. Chem. 2012, 77, 424-431.
2. Shaukat Ali, Hai-Tao Zhu, Xiao-Feng Xia, Ke-Gong Ji, Yan-Fang Yang, Xian-Rong Song, and Yong-Min Liang “Electrophile-Driven Regioselective Synthesis of Functionalized Quinolines” Org. Lett. 2011, 13, 2598-2601.
3. Ying-Xiu Li , Hai-Xi Wang , Shaukat Ali , Xiao-Feng Xia and Yong-Min Liang “Iodine-mediated regioselective C2-amination of indoles and a concise total synthesis of (±)-folicanthine” Chem. Commun. 2012, 48, 2343-2345.
4. Fang Yang, Ke-Gong Ji, Shaukat Ali, and Yong-Min Liang “Sc(OTf)3- Catalyzed Synthesis of Indoles and SnCl4-Mediated Regioselective Hydrochlorination of 5-(Arylamino)pent-3-yn-2-ones” J. Org. Chem. 2011, 76, 8329-8335.
5. Zi-Sheng Chen, Xin-Hua Duan, Ping-Xin Zhou, Shaukat Ali, Jian-Yi Luo, and Yong-Min Liang “Palladium-Catalyzed Divergent Reactions of α-Diazocarbonyl Compounds with Allylic Esters: Construction of Quaternary Carbon Centers” Angew. Chem. Int. Ed. 2012, 51, 1370-1374.
6. Xiao-Feng Xia, Xing-Zhong Shu, Ke-Gong Ji, Yan-Fang Yang, Shaukat Ali, Xue-Yuan Liu, and Yong-Min Liang “Platinum-Catalyzed Michael Addition and Cyclization of Tertiary Amines with Nitroolefins by Dehydrogenation of α,β-sp3 C-H Bonds” J. Org. Chem. 2012, 77, 1616-1616.
7. Hai-Tao Zhu, Ke-Gong Ji, Fang Yang, Li-Jing Wang, Shu-Chun Zhao, Shaukat Ali, Xue-Yuan Liu, and Yong-Min Liang “Electrophilic Carbocyclization of Aryl Propargylic Alcohols: A Facile Synthesis of Diiodinated Carbocycles and Heterocycles” Org. Lett. 2011, 13, 684-687.
8. Ke-Gong Ji, Hai-Tao Zhu, Fang Yang, Shaukat Ali, Xiao-Feng Xia, Yan Fang Yang, Xue-Yuan Liu and Yong-Min Liang “Synthesis of Five- and Six-Membered Dihalogenated Heterocyclic Compounds by Electrophile-Triggered Cyclization” J. Org. Chem. 2010, 75, 5670-5678.
9. Xiao-Feng Xia, Xing-Zhong Shu, Ke-Gong Ji, Shaukat Ali, Xue-Yuan Liu, and Yong-Min Liang “Platinum/Scandium-Cocatalyzed Cascade Cyclization and Ring-Opening Reaction of Tertiary Amines with Substituted Salicylaldehydes to Synthesize 3-(Aminoalkyl)coumarins” J. Org. Chem. 2011, 76, 342-345.
10. Ying-Xiu Li, Ke-Gong Ji, Hai-Xi Wang, Shaukat Ali, and Yong-Min Liang “Iodine-Induced Regioselective C−C and C−N Bonds Formation of N-Protected Indoles” J. Org. Chem. 2011, 76, 744-747.
11. Fang Yang, Ke-Gong Ji, Shu-Chun Zhao, Shaukat Ali, Yu-Ying Ye, Xue- Yuan Liu, Yong-Min Liang “Brønsted Acid Catalyzed Cycloisomerizations of 5,2-Enyne-1-ones: Highly Regioselective Synthesis of 2,3-Dihydro-4H-pyran-4-ones” Chem. Eur. J. 2012, 18, 6470-6474.
12. Yan-Fang Yang, Xing-Zhong Shu, Jian-Yi Luo, Shaukat Ali and Yong- Min Liang “Platinum-Catalyzed Cyclization/[1,2]-Alkyl Migration/Allyl Shift/Cyclization Cascade of Epoxy Alkynyl Allyl Ethers: A Step-Economical Route to Spirobenzo[h]chromanones” Chem. Eur. J. 2012, 18, 8600-8604.
13. Shu-Chun Zhao, Ke-Gong Ji, Lei Lu, Ting He, An-Xi Zhou, Ru-Long Yan, Shaukat Ali, Xue-Yuan, Liu, and Yong-Min Liang “Palladium-Catalyzed Divergent Reactions of 1,6-Enyne Carbonates: Synthesis of Vinylidenepyridines and Vinylidenepyrrolidines” J. Org. Chem. 2012, 77, 2763-2772.
14. Fang Yang, Ke-Gong Ji, Hai-Tao Zhu, Shaukat Ali, Xue-Yuan Liu, and Yong- Min Liang “Electrophilic Carbocyclization of Hydroxylated Enynes” Chem. Eur. J. 2011, 17, 4986-4990.
15. Ke-Gong Ji, Jin Chen, Hai-Tao Zhu, Fang Yang, Shaukat Ali, Yong-Min Liang “Brønsted Acid Catalyzed Cyclization of Hydroxylated Enynes: A Concise Synthesis of Five-Membered Heterocycles” Chem. Eur. J. 2011, 17, 305-311.
16. Zi-Sheng Chen, Xin-Hua Duan, Lu-Yong Wu, Shaukat Ali, Ke-Gong Ji, Ping-Xin Zhou, Xue-Yuan Liu, and Yong-Min Liang “Palladium-Catalyzed Coupling of Propargylic Carbonates with N-Tosylhydrazones: Highly Selective Synthesis of Substituted Propargylic N-Sulfonylhydrazones and Vinylallenes” Chem. Eur. J. 2011, 17, 6918-6921.
17. Yan-Fang Yang, Xing-Zhong Shu, Hai-Long Wei, Jian-Yi Luo, Shaukat Ali, Xue-Yuan Liu and Yong-Min Liang “FeCl3-Mediated synthesis of polysubstituted tetrahydroquinolines via domino Mannich/Friedel–Crafts reactions of aldehydes and amines” Org. Biomol. Chem. 2011, 9, 5028-5033.
18. Xiang-Chuan Wang , Jie Hu , Peng-Shuai Sun , Mei-Jin Zhong , Shaukat Ali and Yong-Min Liang “Copper-catalyzed dimerization fragmentation cyclization reactions of (E)-1-en-4-yn-3-ols as a versatile approach for the synthesis of multisubstituted 1Hcyclopenta[b]naphthalenes” Org. Biomol. Chem. 2011, 9, 7461-7467.
19. Ke-Gong Ji, Hai-Tao Zhu, Fang Yang, Xing-Zhong Shu, Shu-Chun Zhao, Xue-Yuan Liu, Shaukat Ali, and Yong-Min Liang “A Novel Iodine-PromotedTandem Cyclization: An Efficient Synthesis of Substituted 3,4-Diiodoheterocyclic Compounds” Chem. Eur. J. 2010, 16, 6151-6154.
20. Guo-Lin Gao, Yan-Ning Niu, Ze-Yi Yan, Hong-Li Wang, Gang-Wei Wang, Shaukat Ali and Yong-Min Liang “Unexpected Domino Reaction via Pd-Catalyzed Sonogashira Coupling of Benzimidoyl Chlorides with 1,6-Enynes and Cyclization to Synthesize Quinoline Derivatives” J. Org. Chem. 2010, 75, 1305-1308.
21. Fang Yang, Yi-Feng Qiu, Ke-Gong Ji, Yan-Ning Niu, Shaukat Ali, and Yong-Min Liang “Divergent Synthesis of Benzene Derivatives: Bronsted Acid-Catalyzed and Iodine-Promoted Tandem Cyclization of 5, 2-Enyne-1-ones” J. Org. Chem. 2012, 77, 9029-9037.
SCIENTIFIC PRESENTATIONS
Applications of Click Chemistry and other Efficient Organic Reactions in the Synthesis and Functionalization of Polymeric Materials. State Key Laboratory of Polymer Physics and Chemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China, 12th June, 2012.
SKILLS AND ACCOMPLISHMENTS
Expertise in conducting variety of reactions involving low-temperature, inert-handling techniques, moisture sensitive reactions etc.
Well versed in applying spectroscopic techniques viz., NMR, Mass, and IR etc to establish the structural characterization of organic molecules.
Assisting in initiating and look after of projects with under-graduate/graduate students.
Highly experienced in writing scientific publications (articles, communications, letters etc.)