Light-Mediated Synthesis of 2-(4-Methoxyphenyl)-1-pyrroline via Intramolecular Reductive Cyclization of a Triplet Alkylnitrene

被引：3

作者：

George, Sobiya ^{[1
]}

Govorov, Dmitrii ^{[1
]}

Gatlin, DeVonna M. ^{[1
]}

Merugu, Rajkumar ^{[1
]}

Wasson, Fiona J. ^{[1
]}

Shields, Dylan J. ^{[1
]}

Allen, Yasmine ^{[1
]}

Muthukrishnan, Sivaramakrishnan ^{[1
]}

Krause, Jeanette A. ^{[1
]}

Abe, Manabu ^{[2
,3
]}

Gudmundsdottir, Anna D. ^{[1
]}

机构：

[1] Univ Cincinnati, Dept Chem, Cincinnati, OH 45221 USA

[2] Hiroshima Univ, Grad Sch Adv Sci & Engn, Dept Chem, Hiroshima 7398526, Japan

[3] Hiroshima Univ, Int Inst Sustainabil Knotted Chiral Meta Matter WP, Hiroshima 7390046, Japan

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 23期

关键词：

SELECTIVE FORMATION; ALKYL NITRENES; ORGANIC AZIDES; PHOTOLYSIS; ENERGIES; CLEAVAGE;

D O I：

10.1021/acs.orglett.3c01476

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Irradiation of p-methoxyazidobutyrophenone(1) in methanol yielded 2-(4-methoxyphenyl)-1-pyrroline(2) and several other photoproducts. However, in thepresenceof tris-(trimethylsilyl)-silane (TTMSS), 2 is formed selectively.Transient absorption and ESR spectroscopy verify that the irradiationof 1 forms triplet alkylnitrene (3) 1N through intramolecular energy transfer from the triplet ketone (T-1K). DFT calculations indicate that (3) 1N abstracts H atoms from TTMSS but not methanol, which explains theselectivity. Thus, triplet alkylnitrenes can undergo selective reductivecyclization via H atom abstraction from TTMSS.

引用

页码：4345 / 4349

页数：5

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