Rhenium-Catalyzed Cyclization via 1,2-Iodine and 1,5-Hydrogen Migration for the Synthesis of 2-Iodo-1 H-indenes

Masahito Murai; Kazuhiko Takai

doi:10.1021/acs.orglett.9b02380

Rhenium-Catalyzed Cyclization via 1,2-Iodine and 1,5-Hydrogen Migration for the Synthesis of 2-Iodo-1 H-indenes

Masahito Murai, Kazuhiko Takai

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

10 Citations (Scopus)

Abstract

A rhenium complex catalyzed the formation of 2-iodo-1H-indene derivatives through iodine and hydrogen migration of 3-iodopropargyl ethers. The reaction proceeded via generation of 1-iodoalkenylrhenium carbene species by sequential 1,2-iodine and 1,5-hydrogen shifts with readily available precursors under neutral conditions. The reaction mechanism and the reactivity of the generated alkenylcarbene species were also investigated.

Original language	English
Pages (from-to)	6756-6760
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.9b02380
Publication status	Published - Sep 6 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Rhenium-Catalyzed Cyclization via 1,2-Iodine and 1,5-Hydrogen Migration for the Synthesis of 2-Iodo-1 H-indenes",

abstract = "A rhenium complex catalyzed the formation of 2-iodo-1H-indene derivatives through iodine and hydrogen migration of 3-iodopropargyl ethers. The reaction proceeded via generation of 1-iodoalkenylrhenium carbene species by sequential 1,2-iodine and 1,5-hydrogen shifts with readily available precursors under neutral conditions. The reaction mechanism and the reactivity of the generated alkenylcarbene species were also investigated.",

author = "Masahito Murai and Kazuhiko Takai",

note = "Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research (No. 18H03911 and 19H02719) from MEXT, Japan. The authors gratefully thank Jun Namikoshi and Honami Ueda (Okayama University) for work provided on the preliminary study. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.orglett.9b02380",

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AU - Murai, Masahito

AU - Takai, Kazuhiko

N1 - Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research (No. 18H03911 and 19H02719) from MEXT, Japan. The authors gratefully thank Jun Namikoshi and Honami Ueda (Okayama University) for work provided on the preliminary study. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/9/6

Y1 - 2019/9/6

N2 - A rhenium complex catalyzed the formation of 2-iodo-1H-indene derivatives through iodine and hydrogen migration of 3-iodopropargyl ethers. The reaction proceeded via generation of 1-iodoalkenylrhenium carbene species by sequential 1,2-iodine and 1,5-hydrogen shifts with readily available precursors under neutral conditions. The reaction mechanism and the reactivity of the generated alkenylcarbene species were also investigated.

AB - A rhenium complex catalyzed the formation of 2-iodo-1H-indene derivatives through iodine and hydrogen migration of 3-iodopropargyl ethers. The reaction proceeded via generation of 1-iodoalkenylrhenium carbene species by sequential 1,2-iodine and 1,5-hydrogen shifts with readily available precursors under neutral conditions. The reaction mechanism and the reactivity of the generated alkenylcarbene species were also investigated.

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Rhenium-Catalyzed Cyclization via 1,2-Iodine and 1,5-Hydrogen Migration for the Synthesis of 2-Iodo-1 H-indenes

Abstract

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