Merging Rh-catalyzed C-H Functionalization and Cascade Cyclization to Enable Propargylic Alcohols as Three-Carbon Synthons

Prajyot Jayadev Nagtilak, Manoj Vasisht Mane, Supreeth Prasad, Luigi Cavallo, Dean J. Tantillo, Manmohan Kapur

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


Reported herein is a reactivity of propargyl alcohols as “Three-Carbon Synthons” in a Rh(III)-catalyzed C-H functionalization of acetanilides, leading to the synthesis of core structures of isocryptolepine, γ−carbolines, dihydrochromeno[2,3-b]indoles, and diindolylmethanes (DIM) derivatives. The transformation involves a rhodium(III)-catalyzed C-H functionalization and heteroannulation to yield indoles followed by a cascade cyclization with both external and internal nucleophiles to afford diverse products. The role of the hydroxy group, the key function of the silver additive, the origin of the reverse regioselectivity and the rate-determining step, are rationalized in conformity with the combination of experimental, noncovalent interaction analysis and DFT studies. This protocol is endowed with several salient features, including one-pot multistep cascade approach, exclusive regioselectivity, good functional group tolerance and synthesis of variety of molecular frameworks.
Original languageEnglish (US)
JournalChemistry – A European Journal
StatePublished - Oct 5 2022

Bibliographical note

KAUST Repository Item: Exported on 2022-10-07
Acknowledgements: Funding from SERB-India (EMR/2016/004298and STR/2019/000072) and CSIR-Delhi (02(0361)/19/EMR-II) is gratefully acknowledged. PJNthanks CSIR-India, for a research fellowship. We thank Pravin Kumar, IISERB,for solving the X-ray data. We thank the CIF, IISERB, for the analytical data and the Director, IISERB, for funding and the infrastructure facilities. DJT and SP acknowledge computational support from the NSF XSEDE program. MVM, LC acknowledge King Abdullah University of Science and Technology (KAUST) for the Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.

ASJC Scopus subject areas

  • General Chemistry


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