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

共 50 条

[1] [3,3]-Sigmatropic Rearrangement Step in the Gold-Catalyzed Cyclization of Allyl-(ortho-alkinylphenyl)methyl Ethers
Ackermann, Martin
Bucher, Janina
Rappold, Melissa
Graf, Katharina
Rominger, Frank
Hashmi, A. Stephen K.
CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (08) : 1786 - 1794
[2] Generation of allenylthioketene S,S-dioxides through [3,3] sigmatropic rearrangement of alkynyl propargyl sulfones
Aoyagi, Shigenobu
Koyanagi, Makoto
Takahashi, Megumi
Shimada, Kazuaki
Takikawa, Yuji
TETRAHEDRON LETTERS, 2007, 48 (11) : 1915 - 1918
[3] Gold-Catalyzed Addition of N-Hydroxy Heterocycles to Alkynes and Subsequent 3,3-Sigmatropic Rearrangement
Kumar, Manish
Scobie, Martin
Mashuta, Mark S.
Hammond, Gerald B.
Xu, Bo
ORGANIC LETTERS, 2013, 15 (04) : 724 - 727
[4] Total Synthesis of (-)-HM-3 and (-)-HM-4 Using an Asymmetric Gold-Catalyzed [3,3]-Sigmatropic Rearrangement of Sulfonium
Zhou, Weiping
Voituriez, Arnaud
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (17)
[5] Regioselective Cyclizations Utilizing a Gold-Catalyzed [3,3] Propargyl Ester Rearrangement
Cran, John W.
Krafft, Marie E.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (37) : 9398 - 9402
[6] Gold-Catalyzed Reaction of Propargylic Carboxylates via an Initial 3,3-Rearrangement
Wang, Shaozhong
Zhang, Guozhu
Zhang, Liming
SYNLETT, 2010, (05) : 692 - 706
[7] [3,3]-Signiatropic Rearrangement versus Carbene Formation in Gold-Catalyzed Transformations of Alkynyl Aryl Sulfoxides: Mechanistic Studies and Expanded Reaction Scope
Lu, Biao
Li, Yuxue
Wang, Youliang
Aue, Donald H.
Luo, Yingdong
Zhang, Liming
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (23) : 8512 - 8524
[8] 3,3′-Bis(arylbenzofurans) via a Gold-Catalyzed Domino Process
Auzias, Mathieu G.
Neuburger, Markus
Wegner, Hermann A.
SYNLETT, 2010, (16) : 2443 - 2448
[9] A SUBSTITUENT EFFECT ON THE PALLADIUM(II) CATALYZED [3,3]-SIGMATROPIC REARRANGEMENT OF ALLYLIC ESTERS
CHI, KW
KOO, EC
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1994, 15 (02) : 98 - 100
[10] Gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes featuring tandem cyclization and [3,3]-sigmatropic rearrangement
Bae, Hyo J.
Baskar, Baburaj
An, Sang E.
Cheong, Jae Y.
Thangadurai, Daniel T.
Hwang, In-Chul
Rhee, Young H.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2263 - 2266

← 1 2 3 4 5 →