Propargylic Alcohols as Three-Carbon Synthons in a Rhodium-Catalyzed Heteroannulation via a Merged C-H Functionalization and Cascade Cyclization Process

16 February 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report herein, an unprecedented reactivity of propargyl alcohols as a “Three-Carbon Synthon” in the synthesis of core structures of isocryptolepine, g-carbolines, dihydrochromeno[2,3-b]indoles and diindolylmethane's (DIM) derivatives. The transformation involves a rhodium(III)-catalyzed C-H functionalization, heteroannulation of indoles followed by cascade cyclization with external as well as internal nucleophiles to afford diverse products. The reaction features highly effective transformations involving two C-C, two C-N and two C-O bonds, leading to the formation of a variety of molecular frameworks that are a part of several biologically active natural products.

Keywords

C-H functionalization
Rh-Catalyzed
Heteroannulation Reaction
Propargyl alcohols
three-carbon synthons
cascade cyclization process

Supplementary materials

Title
Description
Actions
Title
Prajyot ChemRxiv SI Rh cat heteroannulation Feb21
Description
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