Chemical Science Division, IISc
office.oc@iisc.ac.in

Akkattu T. Biju

Associate Professor

Phone : +91-80-2293-2646(O)
E-mail: atbiju@iisc.ac.in
Home Page : http://atbiju.in/

Biography

Education

  • 2002-2007: Ph. D., Organic Chemistry Division, CSIR-NIIST, Trivandrum, Kerala, mentor: Dr. G. Vijay Nair
  • 1999-2001: M. Sc. Chemistry, MG University, Kottayam, Kerala.
  • 1995-1998: B. Sc. Chemistry (Petrochemicals), MG University, Kottayam, Kerala.

Professional Experience

Research Interests

Transition-Metal-Free Carbon-Carbon and Carbon-Heteroatom Bond-Forming Reactions and their Application in Organic Synthesis

Aryne Chemistry

Arynes are highly electrophilic intermediates, which are widely used for the synthesis of various benzo-fused carbocycles and heterocycles of structural complexity and diversity. In the area of aryne chemistry, we have recently developed mild, efficient and scalable Diels-Alder reaction of arynes with challenging diene systems such as pentafulvenes, 1,2-benzoquinones, styrenes, indenes/ benzofurans, and tropones. Moreover, the synthetic utility of N-heterocycles such as aziridines, pyridines, and (iso)quinolines in aryne multicomponent reactions (MCRs) has been demonstrated for the synthesis of various heterocycles. In addition, we have developed aryne MCRs triggered by phosphines for the synthesis of functionalized benzooxaphospholes, and the use of CO2 as a one-carbon synthon in aryne MCRs has been developed. Furthermore, a transition-metal-free protocol for the N-arylation of tertiary amines as well as the O-arylation of aliphatic alcohols has been developed.

NHC Organocatalysis

In another phase of the work using NHC-catalysis, we have developed efficient and facile Stetter reaction using vinyl sulfones, and vinyl phosphonates as Michael acceptors. Moreover, in the area of homoenolate annulations using NHCs, we have developed efficient methods for the diastereoselective synthesis of cyclopentane-fused coumarins, cyclopentane-fused b-lactones and spirocyclopentanone oxindoles. We are also working on asymmetric catalysis using NHCs. We have recently developed a facile method for the enantioselective synthesis of functionalized dihydropyranones and dihydropyridinones by the reaction of modified enals with b-dicarbonyl compounds or enaminones, enolizable aldehydes, heterocyclic C-H acids, and pyrazolones. Furthermore, an enantioselective synthesis of functionalized cyclopentenes, and b-lactone-fused cyclopentanes by the NHC-catalyzed reaction of 2-bromoenals with a-substituted b-diesters has been uncovered. Very recently, we have also demonstrated the enantioselective synthesis of pyrazolone-fused spirocyclohexadienones by the reaction of a,b-unsaturated aldehydes with a-arylidene pyrazolinones under oxidative NHC-catalysis.

Representative Publications

  • Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes. Werz, D. B.; Biju, A. T. Angew. Chem. Int. Ed. 2020, 59, 3385.
  • N-Heterocyclic Carbene-Catalyzed Umpolung of Imines for the Enantioselective Synthesis of Dihydroquinoxalines. Das, T. K.; Ghosh, A.; Balanna, K.; Behera, P.; Gonnade, R. G.; Marelli, U. K.; Das, A. K.; Biju, A. T. ACS Catal. 2019, 9, 4065.
  • NHC-Catalyzed Generation of α,β-Unsaturated Acylazoliums for the Enantioselective Synthesis of Heterocycles and Carbocycles. Mondal, S.; Yetra, S. R.; Mukherjee, S.; Biju, A. T. Acc. Chem. Res. 2019, 52, 425.
  • N-Heterocyclic Carbene-Catalyzed Aldol-Lactonization of Ketoacids via Dynamic Kinetic Resolution. Mondal, S.; Mukherjee, S.; Das, T. K.; Gonnade, R. G.; Biju, A. T. ACS Catal. 2017, 7, 3995.
  • N-Heterocyclic Carbene-Catalyzed Umpolung of Imines, Patra, A.; Mukherjee, S.; Das, T. K.; Jain, S.; Gonnade, R. G.; Biju, A. T. Angew. Chem. Int. Ed. 2017, 56, 2730.
  • Employing Arynes in Transition-Metal-Free Carbon-Carbon and Carbon-Heteroatom Bond-Forming Reactions. Bhojgude, S. S.; Bhunia, A.; Biju, A. T. Acc. Chem. Res. 2016, 49, 1658.
  • Lewis Acid-Catalyzed Selective Reactions of Donor-Acceptor Cyclopropanes with 2-Naphthols. Kaicharla, T.; Roy, T.; Thangaraj, M.; Gonnade, R. G.; Biju, A. T. Angew. Chem. Int. Ed. 2016, 55, 10061.
  • Enantioselective Synthesis of Spirocyclohexadienones by NHC-Catalyzed Formal [3+3] Annulation Reaction of Enals. Yetra, S. R.; Mondal, S.; Mukherjee, S.; Gonnade. R. G.; Biju, A. T. Angew. Chem. Int. Ed. 2016, 55, 268.
  • Transition-Metal-Free Multicomponent Reactions Involving Arynes, N-Heterocycles and Isatins. Bhunia, A.; Roy, T.; Pachfule, P.; Rajamohanan, P. R.; Biju, A. T. Angew. Chem., Int. Ed. 2013, 52, 10040.
  • Recent Advances in Transition-Metal-Free Carbon-Carbon and Carbon-Heteroatom Bond-Forming Reactions Using Arynes. Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140.
  • Arynes in Transition-Metal-Free Multicomponent Coupling Reactions. Bhojgude, S. S.; Biju, A. T. Angew. Chem., Int. Ed. 2012, 51, 1520.

Awards / Honours / Affiliations