C-O Functionalization of alpha-Oxyboronates: A Deoxygenative gem-Diborylation and gem-Silylborylation of Aldehydes and Ketones | |
Department | 苏州研究院 |
Wang L(王露)1; Zhang, Tao1,2; Sun W(孙威)1; He, Zeyu1; Xia CG(夏春谷)1; Lan, Yu2; Liu C(刘超)1; Liu C(刘超) | |
The second department | osso国家重点实验室 |
2017 | |
Source Publication | Journal of the American Chemical Society |
ISSN | 0002-7863 |
Volume | 139Issue:14Pages:5257-5264 |
Abstract | A deoxygenative gem-diborylation and gem-silylborylation of aldehydes and ketones is described. The key for the success of this transformation is the base-promoted C–O bond borylation or silylation of the generated α-oxyboronates. Experimental and theoretical studies exhibit that the C–O bond functionalization proceeds via an intramolecular five-membered transition-state (9-ts) boryl migration followed by a 1,2-metalate rearrangement with OBpin as a leaving group. The transformation occurs with an inversion on the carbon center. Direct conversion of aldehydes and ketones to gem-diboron compounds was achieved by combining copper catalysis with this base-promoted C-OBpin borylation. Various aldehydes and ketones were deoxygenatively gem-diborylated. gem-Silylborylation of aldehydes and ketones were achieved by a stepwise operation, in which B2pin2 initially react with those carbonyls followed by a silylation with Bpin-SiMe2Ph. |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1021/jacs.7b02518 |
Funding Organization | the National Natural Science Foundation of China (21673261;21603245;21633013;21372266);the State Key Laboratory for Oxo Synthesis and Selective Oxidation (OSSO), Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences;CAS Interdisciplinary Innovation Team |
Indexed By | SCI |
If | 13.858 |
Language | 英语 |
Funding Project | 均相催化研究组 |
compositor | 第一作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/21783 |
Collection | 苏州研究院 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Lan, Yu; Liu C(刘超) |
Affiliation | 1.Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China 2.Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China |
Recommended Citation GB/T 7714 | Wang L,Zhang, Tao,Sun W,et al. C-O Functionalization of alpha-Oxyboronates: A Deoxygenative gem-Diborylation and gem-Silylborylation of Aldehydes and Ketones[J]. Journal of the American Chemical Society,2017,139(14):5257-5264. |
APA | Wang L.,Zhang, Tao.,Sun W.,He, Zeyu.,Xia CG.,...&刘超.(2017).C-O Functionalization of alpha-Oxyboronates: A Deoxygenative gem-Diborylation and gem-Silylborylation of Aldehydes and Ketones.Journal of the American Chemical Society,139(14),5257-5264. |
MLA | Wang L,et al."C-O Functionalization of alpha-Oxyboronates: A Deoxygenative gem-Diborylation and gem-Silylborylation of Aldehydes and Ketones".Journal of the American Chemical Society 139.14(2017):5257-5264. |
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