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

2 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.",

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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.

PY - 2019/9/6

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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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