[4+2] Cycloaddition of o-xylylenes with imines using palladium catalyst

Satoshi Ueno; Masakazu Ohtsubo; Ryoichi Kuwano

doi:10.1021/ja905988e

[4+2] Cycloaddition of o-xylylenes with imines using palladium catalyst

Satoshi Ueno, Masakazu Ohtsubo, Ryoichi Kuwano

複合領域化学

研究成果: Contribution to journal › Article › 査読

30 被引用数 (Scopus)

抄録

(Chemical Equation Presented) The cycloaddition of o-(silylmethyl)benzylic carbonates with imines proceeded in the presence of the Pd(η³- C₃H₅)Cp-DPPPent catalyst, affording the tetrahydroisoquinolines in good to high yields. The reaction rate was remarkably increased by a fluoride additive. In the catalytic cycloaddition, the palladium(0) reacted with the benzylic substrate to form 2-palladaindane, which works as an o-xylylene equivalent. The catalytic reaction is equivalent to the hetero-Diels-Alder reaction of o-xylylene with imines.

本文言語	英語
ページ（範囲）	12904-12905
ページ数	2
ジャーナル	Journal of the American Chemical Society
巻	131
号	36
DOI	https://doi.org/10.1021/ja905988e
出版ステータス	出版済み - 9 16 2009

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

文献へのアクセス

10.1021/ja905988e

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引用スタイル

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abstract = "(Chemical Equation Presented) The cycloaddition of o-(silylmethyl)benzylic carbonates with imines proceeded in the presence of the Pd(η3- C3H5)Cp-DPPPent catalyst, affording the tetrahydroisoquinolines in good to high yields. The reaction rate was remarkably increased by a fluoride additive. In the catalytic cycloaddition, the palladium(0) reacted with the benzylic substrate to form 2-palladaindane, which works as an o-xylylene equivalent. The catalytic reaction is equivalent to the hetero-Diels-Alder reaction of o-xylylene with imines.",

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AB - (Chemical Equation Presented) The cycloaddition of o-(silylmethyl)benzylic carbonates with imines proceeded in the presence of the Pd(η3- C3H5)Cp-DPPPent catalyst, affording the tetrahydroisoquinolines in good to high yields. The reaction rate was remarkably increased by a fluoride additive. In the catalytic cycloaddition, the palladium(0) reacted with the benzylic substrate to form 2-palladaindane, which works as an o-xylylene equivalent. The catalytic reaction is equivalent to the hetero-Diels-Alder reaction of o-xylylene with imines.

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