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Correction: Palladium-catalysed 5-endo-trig allylic (hetero)arylation

Bara Singh , Siddheshwar K. Bankar , Ketan Kumar and S. S. V. Ramasastry *
Organic Synthesis and Catalysis Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Sector 81, Manauli PO, S. A. S. Nagar, Punjab 140306, India. E-mail:;

Received 4th August 2020 , Accepted 4th August 2020

First published on 14th August 2020

Correction for ‘Palladium-catalysed 5-endo-trig allylic (hetero)arylation’ by Bara Singh et al., Chem. Sci., 2020, 11, 4948–4953, DOI: 10.1039/D0SC01932A.

After the publication of our manuscript, a reader suggested that the transformation (shown in Scheme 1) can also be described as a Nazarov-type cyclisation1 with palladium chloride acting as a Lewis acid. While we do not have any evidence at this stage to support the Lewis acidic behaviour of palladium chloride,2 however, a Nazarov-type mechanistic scenario is possible. The overall transformation can also be considered as an intramolecular ene-type reaction3 or as an intramolecular Friedel–Crafts-type reaction,4 although our data agrees better with the 5-endo-trig process facilitated by the LUMO umpolung.5 Further experimental and computational investigations are underway to elucidate the full mechanistic details.
image file: d0sc90169e-s1.tif
Scheme 1 General representation of the palladium-catalysed intramolecular allylic (hetero)arylation strategy reported by our group.

We thank the reader for the thought-provoking comments and also for their interest in our work.

Previously, the methoxy (–OMe) groups in the structure 2l (Table 2) were wrongly placed. The correct structure of 2l is show below.

image file: d0sc90169e-u1.tif

These corrections do not influence any conclusions reported in the main article.

The Royal Society of Chemistry apologises for these errors and any consequent inconvenience to authors and readers.


  1. For some seminal contributions on Nazarov-type cyclisation reactions, see: (a) C. Bee, E. Leclerc and M. A. Tius, Org. Lett., 2003, 5, 4927 CrossRef CAS PubMed; (b) A. J. Frontier and C. Collison, Tetrahedron, 2005, 61, 7577 CrossRef CAS; (c) J. A. Malona, J. M. Colbourne and A. J. Frontier, Org. Lett., 2006, 8, 5661 CrossRef CAS PubMed; (d) S. S. Subramanium, S. Handa, A. J. Miranda and L. M. Slaughter, ACS Catal., 2011, 1, 1371 CrossRef CAS; (e) W. T. Spencer, T. Vaidya and A. J. Frontier, Eur. J. Org. Chem., 2013, 3621 CrossRef CAS PubMed; (f) J. Shao, P. Hu, G. Hong, M. Fang, X. Li and X. Xu, Synlett, 2014, 25, 1009 CrossRef CAS; (g) T. Vaidya, R. Cheng, P. N. Carlsen, A. J. Frontier and R. Eisenberg, Org. Lett., 2014, 16, 800 CrossRef CAS PubMed; (h) K. Kitamura, N. Shimada, C. Stewart, A. C. Atesin, T. A. Atesin and M. A. Tius, Angew. Chem., Int. Ed., 2015, 54, 6288 CrossRef CAS PubMed; (i) M. C. Martin, M. J. Sandridge, C. W. Williams, Z. A. Francis and S. France, Tetrahedron, 2017, 73, 4093 CrossRef CAS.
  2. For some rare examples where palladium(II) complexes were shown to behave as Lewis acids, see: (a) N. Asao, T. Nogami, K. Takahashi and Y. Yamamoto, J. Am. Chem. Soc., 2002, 124, 764 CrossRef CAS PubMed; (b) Y. Xiao and J. Zhang, Angew. Chem., Int. Ed., 2008, 47, 190 CrossRef PubMed.
  3. (a) S. K. Bankar, B. Singh, P. Tung and S. S. V. Ramasastry, Angew. Chem., Int. Ed., 2018, 57, 1678 CrossRef CAS PubMed; (b) S. Yadav, R. Hazra, A. Singh and S. S. V. Ramasastry, Org. Lett., 2019, 21, 2983 CrossRef CAS PubMed.
  4. (a) J. S. Yadav, A. K. Mishra and S. Das, Tetrahedron, 2014, 70, 7560 CrossRef CAS; (b) Z.-L. Zhao, Q. L. Xu, Q. Gu, X.-Y. Wu and S.-L. Yu, Org. Biomol. Chem., 2015, 13, 3086 RSC; (c) T. Nemato and Y. Hamada, Synlett, 2016, 27, 2301 CrossRef.
  5. According to the pioneer in this field, Prof. Igor Alabugin, the LUMO umpolung would apply to olefins as long as the π-complex formation is feasible. For details, see: (a) I. V. Alabugin and K. Gilmore, Chem. Commun., 2013, 49, 11246 RSC; (b) G. dos Passos Gomes and I. V. Alabugin, J. Am. Chem. Soc., 2017, 139, 3406 CrossRef CAS PubMed; (c) I. V. Alabugin and E. Gonzalez-Rodriguez, Acc. Chem. Res., 2018, 51, 1206 CrossRef CAS PubMed.

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