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A highly efficient precatalytic system (XPhos-PdG2) for the Suzuki–Miyaura cross-coupling of 7-chloro-1H-pyrrolo[2,3-c]pyridine employing low catalyst loading

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Abstract

An expedient catalytic method for the synthesis of diverse 7-(hetero) aryl-1H-pyrrolo[2,3-c]pyridine analogues via microwave-assisted Suzuki–Miyaura cross-coupling reaction with excellent yield was developed. The method is found to be compatible with various boronic acids and potassium organotrifluoroborates. The formation of highly stable monoligated catalytic species is found to be instrumental in driving the reactions to excellent conversions in Suzuki–Miyaura coupling. Herein, we report our findings on the use of a highly efficient precatalytic system (XPhos-PdG2), containing a bulky monodentate biaryl ligand which allows the rapid reductive elimination to form the true monoligated Pd(0) catalytic species, thereby facilitating the Suzuki coupling reaction of 7-chloro, 6-azaindole system containing unprotected free N–H group with excellent conversions employing low catalyst loadings. Also, we observed that the use of near stoichiometric potassium organotrifluoroborate reagents as alternative coupling partners for boronic acids, which are prone to protodeboronation, resulted in excellent conversions.

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Authors and Affiliations

  1. Postgraduate and Research Department of Chemistry, Jamal Mohamed College, Bharathidasan University, Tiruchirappalli, Tamil Nadu, 620020, India

    Bhaskaran Savitha, D. Parthasarathi & M. Syed Ali Padusha

  2. Department of Chemistry, Vignan’s Foundation for Science, Technology and Research –VFSTR (Deemed to be University), Vadlamudi, Guntur, Andhra Pradesh, 522 213, India

    Eeda Koti Reddy

  3. School of Chemical Sciences, Kannur University, Payyanur Campus, Edat P.O., Kannur, Kerala, 670327, India

    Rajeesh Pakkath, Ranjith Pakkath Karuvalam & K. R. Haridas

  4. Postgraduate and Research Department of Chemistry, Kasaragod Government College, Kannur University, Kasaragod, Kerala, 671123, India

    Ayyiliath M. Sajith

  5. Visvesvaraya Technological University, CPGS, Muddenahalli, 562 101, India

    C. S. Ananda Kumar

  6. Centre for Material Science, University of Mysore, Mysore, 570 006, India

    C. S. Ananda Kumar

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  1. Bhaskaran Savitha
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  8. M. Syed Ali Padusha
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Correspondence to M. Syed Ali Padusha or Ayyiliath M. Sajith.

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Savitha, B., Reddy, E.K., Parthasarathi, D. et al. A highly efficient precatalytic system (XPhos-PdG2) for the Suzuki–Miyaura cross-coupling of 7-chloro-1H-pyrrolo[2,3-c]pyridine employing low catalyst loading. Mol Divers 23, 697–707 (2019). https://doi.org/10.1007/s11030-018-9904-6

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