Divergent reactivity of sulfoxonium ylide with allyl carbonate and allyl carbamate

Vinayak Hanchate; Sudharshan Nagabhushana Reddy; Anil Kumar; Kandikere Ramaiah Prabhu

doi:10.1039/d3cc01657a

Divergent reactivity of sulfoxonium ylide with allyl carbonate and allyl carbamate

Vinayak Hanchate, Sudharshan Nagabhushana Reddy, Anil Kumar, Kandikere Ramaiah Prabhu

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

A divergent reactivity of sulfoxonium ylide with allyl carbonates and allyl carbamates is demonstrated. Rh(iii)-catalyzed C-H activation and cyclization of sulfoxonium ylide with ally esters leads to the formation of a cyclopropane-fused tetralone derivative by cascade C-H activation, (4+2) annulation, and cyclopropanation. A similar reaction of sulfoxonium ylide with allyl carbamates forms a C3-substituted indanone derivative via a rare and interesting domino C-H activation and (4+1) annulation in which allyl carbamate is acting as a C1-synthon.

Original language	English (US)
Pages (from-to)	9223-9226
Number of pages	4
Journal	Chemical Communications
Volume	59
Issue number	60
DOIs	https://doi.org/10.1039/d3cc01657a
State	Published - Jun 28 2023
Externally published	Yes

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Divergent reactivity of sulfoxonium ylide with allyl carbonate and allyl carbamate",

abstract = "A divergent reactivity of sulfoxonium ylide with allyl carbonates and allyl carbamates is demonstrated. Rh(iii)-catalyzed C-H activation and cyclization of sulfoxonium ylide with ally esters leads to the formation of a cyclopropane-fused tetralone derivative by cascade C-H activation, (4+2) annulation, and cyclopropanation. A similar reaction of sulfoxonium ylide with allyl carbamates forms a C3-substituted indanone derivative via a rare and interesting domino C-H activation and (4+1) annulation in which allyl carbamate is acting as a C1-synthon.",

author = "Vinayak Hanchate and Reddy, {Sudharshan Nagabhushana} and Anil Kumar and Prabhu, {Kandikere Ramaiah}",

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T1 - Divergent reactivity of sulfoxonium ylide with allyl carbonate and allyl carbamate

AU - Hanchate, Vinayak

AU - Reddy, Sudharshan Nagabhushana

AU - Kumar, Anil

AU - Prabhu, Kandikere Ramaiah

PY - 2023/6/28

Y1 - 2023/6/28

N2 - A divergent reactivity of sulfoxonium ylide with allyl carbonates and allyl carbamates is demonstrated. Rh(iii)-catalyzed C-H activation and cyclization of sulfoxonium ylide with ally esters leads to the formation of a cyclopropane-fused tetralone derivative by cascade C-H activation, (4+2) annulation, and cyclopropanation. A similar reaction of sulfoxonium ylide with allyl carbamates forms a C3-substituted indanone derivative via a rare and interesting domino C-H activation and (4+1) annulation in which allyl carbamate is acting as a C1-synthon.

AB - A divergent reactivity of sulfoxonium ylide with allyl carbonates and allyl carbamates is demonstrated. Rh(iii)-catalyzed C-H activation and cyclization of sulfoxonium ylide with ally esters leads to the formation of a cyclopropane-fused tetralone derivative by cascade C-H activation, (4+2) annulation, and cyclopropanation. A similar reaction of sulfoxonium ylide with allyl carbamates forms a C3-substituted indanone derivative via a rare and interesting domino C-H activation and (4+1) annulation in which allyl carbamate is acting as a C1-synthon.

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Divergent reactivity of sulfoxonium ylide with allyl carbonate and allyl carbamate

Abstract

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