Stereoselective Preparation and Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkenyl Sulfoximines

Yasui, Kosuke; Tomishima, Yuichiro; Miura, Tomoya et al.

Angewandte Chemie - International Edition, 2025, e202420949

Number of Access:388（2025-07-17 20:56 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/100540

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Title
Stereoselective Preparation and Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkenyl Sulfoximines
Creator
NRID
1000010877640 1000010877640
ORCID
0000-0002-3906-8307 0000-0002-3906-8307
researchmap permalink
k_yasui k_yasui
CreatorName
Yasui, Kosuke
CreatorName
Tomishima, Yuichiro
NRID
1000010378804 1000010378804
CreatorName
Miura, Tomoya
NRID
1000000963315 1000000963315
CreatorName
Yamazaki, Ken
NRID
1000070532696 1000070532696
ORCID
0000-0001-9752-1985 0000-0001-9752-1985
researchmap permalink
koj koj
Scopus Author ID
7402407063 7402407063
CreatorName
Hirano, Koji
Subject
Condensation
Cross-coupling
Stereoselectivity
Sulfoximines
Trisubstituted alkenes
Description
Yasui K., Tomishima Y., Miura T., et al. Stereoselective Preparation and Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkenyl Sulfoximines. Angewandte Chemie - International Edition, (2025); https://doi.org/10.1002/anie.202420949.
Abstract
Although numerous transition-metal catalyzed cross-coupling reactions of alkenyl electrophiles with a sulfur(VI) leaving group, mainly alkenyl sulfones, have been developed, most rely heavily on highly nucleophilic Grignard reagents, and the use of organoboron reagents remains challenging. We report herein facile preparation and the following Pd-catalyzed Suzuki–Miyaura cross-coupling reaction of alkenyl sulfoximine, a monoaza analog of sulfone. The condensation of alkyl sulfoximine with aldehydes, developed in this study, makes alkenyl sulfoximines more readily available. The resulting alkenes undergo an unprecedented oxidative addition of the C−S bond to the Pd center. This cross-coupling proceeds with retention of its original stereochemistry and provided alkenes bearing three different functionalities in a stereoselective fashion. DFT calculations highlight the critical role of boronic acid and in situ-generated boroxines in facilitating this transformation.
Publisher
John Wiley and Sons Inc
Source Title
Angewandte Chemie - International Edition
Page
e202420949
Date of Issued
2025-02-14
Language
English
Handle URL
https://hdl.handle.net/11094/100540
PISSN
14337851
eISSN
15213773
Relation.isIdenticalTo
DOI (Publisher Version)
https://doi.org/10.1002/anie.202420949
Access Rights
open access
CopyRight
This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
oaire:version
Version of Record
Category
学術雑誌論文 Journal Article