Rhodium-catalyzed annulation reactions of 2-cyanophenylboronic acid with alkynes and strained alkenes

Tomoya Miura; Masahiro Murakami

doi:10.1021/ol051249u

Rhodium-catalyzed annulation reactions of 2-cyanophenylboronic acid with alkynes and strained alkenes

Tomoya Miura, Masahiro Murakami

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

93 Citations (Scopus)

Abstract

(Chemical Equation Presented) A new [3 + 2] annulation reaction was developed in which 2-cyanophenylboronic acid reacted as a three-carbon component with alkynes or alkenes to afford substituted indenones or indanones. The use of an alkynoate even produced benzotropone, a formal [3 + 2 + 2] adduct. The cyclic skeletons were constructed by intramolecular nucleophilic addition of an intermediate organorhodium(I) species to a cyano group.

Original language	English
Pages (from-to)	3339-3341
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	15
DOIs	https://doi.org/10.1021/ol051249u
Publication status	Published - Jul 21 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol051249u

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abstract = "(Chemical Equation Presented) A new [3 + 2] annulation reaction was developed in which 2-cyanophenylboronic acid reacted as a three-carbon component with alkynes or alkenes to afford substituted indenones or indanones. The use of an alkynoate even produced benzotropone, a formal [3 + 2 + 2] adduct. The cyclic skeletons were constructed by intramolecular nucleophilic addition of an intermediate organorhodium(I) species to a cyano group.",

author = "Tomoya Miura and Masahiro Murakami",

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AU - Murakami, Masahiro

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N2 - (Chemical Equation Presented) A new [3 + 2] annulation reaction was developed in which 2-cyanophenylboronic acid reacted as a three-carbon component with alkynes or alkenes to afford substituted indenones or indanones. The use of an alkynoate even produced benzotropone, a formal [3 + 2 + 2] adduct. The cyclic skeletons were constructed by intramolecular nucleophilic addition of an intermediate organorhodium(I) species to a cyano group.

AB - (Chemical Equation Presented) A new [3 + 2] annulation reaction was developed in which 2-cyanophenylboronic acid reacted as a three-carbon component with alkynes or alkenes to afford substituted indenones or indanones. The use of an alkynoate even produced benzotropone, a formal [3 + 2 + 2] adduct. The cyclic skeletons were constructed by intramolecular nucleophilic addition of an intermediate organorhodium(I) species to a cyano group.

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Rhodium-catalyzed annulation reactions of 2-cyanophenylboronic acid with alkynes and strained alkenes

Abstract

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