Gold-Catalyzed [3,3]-Sigmatropic Rearrangement of ortho-Alkynyl-S,S-diarylsulfi limines

被引：8

作者：

Mackenroth, Alexandra, V ^{[1
]}

Antoni, Patrick W. ^{[1
]}

Rominger, Frank ^{[1
]}

Rudolph, Matthias ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Organ Chem Inst, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Fac Sci, Chem Dept, Jeddah 21589, Saudi Arabia

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 16期

关键词：

DERIVATIVES; SULFONIUM;

D O I：

10.1021/acs.orglett.3c00953

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly functionalized 5H-pyrrolo[2,3-b]pyrazine cores, carrying a diaryl sulfide moiety at the C-7 position, were obtained from a gold-catalyzed reaction using easily accessible ortho-alkynyl-substituted S,S-diarylsulfilimines as intramolecular nitrene transfer reagents for the first time. The reaction proceeds under mild conditions, providing excellent yields while tolerating a large variety of different substitution patterns. We provide experimental evidence for an intramolecular reaction mechanism, likely including an unprecedented gold-catalyzed amino sulfonium [3,3]-sigmatropic rearrangement.

引用

页码：2907 / 2912

页数：6

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