https://scholar.dgist.ac.kr/handle/20.500.11750/12074 2026-05-14T23:31:11Z 2026-05-14T23:31:11Z Lee, Yeonjoo Kim, Minseop Lee, Dohun Lee, Yunmi Seo, Sangwon Jung, Byunghyuck https://scholar.dgist.ac.kr/handle/20.500.11750/60350 2026-05-11T08:10:13Z 2026-02-28T15:00:00Z

Title: Cu-Catalyzed Stereo- and Regioselective Diborylation and trans-Protoborylation of 1,3-Enynes Author(s): Lee, Yeonjoo; Kim, Minseop; Lee, Dohun; Lee, Yunmi; Seo, Sangwon; Jung, Byunghyuck Abstract: As multifunctional chemical tools, organodiboron compounds present an important challenge in organic synthesis, with respect to their synthesis and functionalization. Although readily available 1,3-enynes have been employed as a platform for various regioselective difunctionalization reactions, the diborylation reactions of 1,3-enynes remain limited, and the installation of a CF3 group is often a prerequisite. In this study, we report a copper-catalyzed selective diborylation reaction of 1,3-enynes to access synthetically useful 1,1- and 1,4-diborylalkenes. The synthetic utility of this method is demonstrated by a gram-scale synthesis of a natural antifouling agent. Furthermore, the Cu-catalyzed trans-protoborylation reaction of aryl-substituted (Z)-enynes is reported. The thorough computational studies and the deuterium-labeling experiments provide insights into the reaction mechanism and the regio- and stereoselectivity of diborylated products.

2026-02-28T15:00:00Z Kim, Gun Ha Jeon, Ji Hwan Jung, Byunghyuck Rohde, Jan-Uwe Hong, Sung You https://scholar.dgist.ac.kr/handle/20.500.11750/58586 2025-12-18T02:41:23Z 2025-07-31T15:00:00Z

Title: Regioselective Transformations of Unsaturated Systems Catalyzed by Low-Valent Nickel: Cycloaddition, Hydrosilylation, and Dicarbofunctionalization Author(s): Kim, Gun Ha; Jeon, Ji Hwan; Jung, Byunghyuck; Rohde, Jan-Uwe; Hong, Sung You Abstract: In this Account, we describe our recent research progress in the development of the functionalization of unsaturated substrates catalyzed by low-valent nickel. In particular, we discuss nickel-catalyzed azide–alkyne cycloaddition (NiAAC), [2 + 2 + 2] cycloaddition of diynes and nitriles, hydrosilylation of alkynes, and dicarbofunctionalization of 1,3-enynes. Moreover, we highlight our mechanistic studies aimed at elucidating catalytically active nickel intermediates, thereby contributing to the understanding and expansion of nickel-catalyzed synthetic methodologies. © 2025. Thieme. All rights reserved.

2025-07-31T15:00:00Z Kim, Min Kim, Seongha Lee, Yurim Lee, Yunmi Seo, Sangwon Jung, Byunghyuck https://scholar.dgist.ac.kr/handle/20.500.11750/58224 2025-12-18T02:42:23Z 2024-12-31T15:00:00Z

Title: Synthesis of (Z)-Allylsilanes by Cu-Catalyzed Regioselective Protosilylation of Allenes via a Single-Electron Process Author(s): Kim, Min; Kim, Seongha; Lee, Yurim; Lee, Yunmi; Seo, Sangwon; Jung, Byunghyuck Abstract: Hydrosilylation of allenes has gained prominence as an economically viable method for preparing vinylsilanes or allylsilanes. However, development of transition metal (TM)-catalyzed hydrosilylation remains challenging owing to the difficulty in controlling the regioselectivity and stereoselectivity. Specifically, access to (Z)-allylsilanes via first-row TM-catalyzed hydrosilylation is limited by the lack of mechanistic diversity, indicating the need for unprecedented approaches to achieve this valuable yet underexplored chemical space. We herein present the Cu-catalyzed protosilylation of allenes in either organic solvent or water, which affords (Z)-allylsilanes in high yields, with up to >98:2 regioselectivity and (Z)-selectivity. In contrast to conventional TM-catalyzed hydrosilylation or Cu-catalyzed protosilylation, our process involves a single-electron pathway for inserting Cu-SiMe2Ph into the allene. Radical trap experiments and systematic computational studies support the proposed mechanism. Our method is gram-scalable, and the synthetic utility is demonstrated by the preparation of deuterium-incorporated (Z)-allylsilanes through reactions in D2O.

2024-12-31T15:00:00Z Park, Cheong Hoon Lim, Seeun Jung, Byunghyuck Lee, Yunmi https://scholar.dgist.ac.kr/handle/20.500.11750/58159 2025-07-25T03:36:47Z 2025-03-31T15:00:00Z

Title: Regioselective Formal Hydroamidation of Alkynes: Synthesis of α-Substituted Acrylamides Author(s): Park, Cheong Hoon; Lim, Seeun; Jung, Byunghyuck; Lee, Yunmi Abstract: The formal hydroamidation of alkyne is a powerful synthetic method that enables the formation of various α,β-unsaturated amides. In this article, the efficient formal hydroamidation of terminal and internal alkynes is described, which constitutes the Ni-catalyzed α-selective hydroalumination of alkynes and subsequent treatment with isocyanates. This method is gram-scalable and the synthetic utility is highlighted by the synthesis of a β-lactam from α-phenyl acrylamide. © 2025 Wiley-VCH GmbH.

2025-03-31T15:00:00Z