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

アクセス数:404件（2025-07-27 09:07 集計）

固定URL: https://hdl.handle.net/11094/100540

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タイトル
Stereoselective Preparation and Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkenyl Sulfoximines
著者
NRID
1000010877640 1000010877640
ORCID
0000-0002-3906-8307 0000-0002-3906-8307
researchmap permalink
k_yasui k_yasui
著者名
Yasui, Kosuke
著者名
Tomishima, Yuichiro
NRID
1000010378804 1000010378804
著者名
Miura, Tomoya
NRID
1000000963315 1000000963315
著者名
Yamazaki, Ken
NRID
1000070532696 1000070532696
ORCID
0000-0001-9752-1985 0000-0001-9752-1985
researchmap permalink
koj koj
Scopus Author ID
7402407063 7402407063
著者名
Hirano, Koji
キーワード等
Condensation
Cross-coupling
Stereoselectivity
Sulfoximines
Trisubstituted alkenes
内容
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.
抄録
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.
出版者
John Wiley and Sons Inc
収録物名
Angewandte Chemie - International Edition
ページ
e202420949
刊行年月
2025-02-14
言語
英語
ハンドルURL
https://hdl.handle.net/11094/100540
PISSN
14337851
eISSN
15213773
関連情報 (isIdenticalTo)
DOI (出版社版)
https://doi.org/10.1002/anie.202420949
アクセス権
open access
権利情報
This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
出版タイプ
Version of Record
カテゴリ
学術雑誌論文 Journal Article