Enantioselective Copper-Catalyzed Defluoroalkylation Using Arylboronate-Activated Alkyl Grignard Reagents

Wang, Minyan; Pu, Xinghui; Zhao, Yunfei; Wang, Panpan; Li, Zexian; Zhu, Chendan; Shi, Zhuangzhi

doi:10.1021/jacs.8b04902

Cited by 144 publications

(50 citation statements)

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“…Catalytic EAS with E ‐trifluoromethyl‐substituted olefins was disclosed by Shi in 2018 (Scheme 23). [50] The Cu complex derived from imid(S)‐2 c was the most effective. Inclusion of PhB(neo) (neo=neopentyl glycolate) improved yield and e.r., likely because the borate is the alkylating agent [51] …”

Section: Catalytic Enantioselective Allylic Substitution (Eas)mentioning

confidence: 98%

Sulfonate N‐Heterocyclic Carbene–Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C−C, C−B, C−H, and C−Si Bonds

et al. 2020

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…I believe that every militant chemist can confirm it:that one must distrust the almost-the-same…, the practically identical, the approximate, the or-even, all surrogates and all patchwork. The differences can be small, but they can lead to radically different consequences…; the chemist's trade consists in good part in being aware of these differences, knowing them close up, and foreseeing their effects. "

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Section: Catalytic Enantioselective Allylic Substitution (Eas)mentioning

confidence: 98%

Sulfonate N‐Heterocyclic Carbene–Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C−C, C−B, C−H, and C−Si Bonds

et al. 2020

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“…In 2018, our group succeeded in enantioselective coppercatalyzed defluoroalkylation of 1-trifluoromethylalkenes by using chiral N-heterocyclic carbene (NHC) 7 as ligand, where the arylboronate-activated alkyl Grignard reagents were first employed as alkyl source (Scheme 5). 11 Aryl and heteroaryl substituted allylic fluorides were treated with EtMgBr, and various gem-difluoroalkenes were synthesized effeciently with high enantioselectivity in moderate to excellent yields. Grignard reagents with longer alkyl chains or bulky steric groups were also tolerated under the optimized conditions, while the enantioselective defluoroalkylation with t BuMgCl and MeMgBr failed.…”

Section: Enantioselective Defluoroalkylationmentioning

confidence: 99%

Catalytic Enantioselective Allylic C–F Bond Functionalization

Wang

Shi

2020

Chemistry Letters

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Minyan Wang was born in Henan province, People's Republic of China. She obtained her B.S. degree in applied chemistry from Huazhong University of Science and Technology in 2009. Then, she moved to Zhejiang University and finished her Ph.D. in organic chemistry with Prof. Shengming Ma. In 2014, she joined the group of Prof. Lukas Gooßen at TU Kaiserslautern (Germany) as a postdoctoral fellow. She joined Nanjing University at the end of 2016 and was promoted to associate professor in 2019. Her research interests include asymmetric synthetic chemistry and computational chemistry. Zhuangzhi Shi was born in Jiangsu province, People's Republic of China, in 1983. He received his B.S. and M.S. degrees in chemistry and organic chemistry from Yangzhou University in 2005 and 2008. Then, he moved to Peking University and completed his Ph.D. in medicinal chemistry with Prof. Ning Jiao. In 2011, he joined the group of Prof. Frank Glorius at Westfalische Wilhelms-Universitat Münster (Germany), as an Alexander von Humboldt Research Fellow. In 2014, he joined the faculty at Nanjing University as a full professor. His current research efforts are focused on synthetic methodology, including the activation of inert chemical bonds, radical chemistry, boron chemistry and asymmetric catalysis.

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“…30 Another major challenge for these substrates is that nucleophilic addition to trifluoromethyl alkenes often suffers from the defluorinations. 28,[31][32][33] In terms of boron chemistry, transition-metal (TM)-catalyzed defluoroborylation of trifluoromethyl alkenes would exclusively generate the gem-difluoroallylboronates (Figure 1C). [34][35][36][37][38][39] Despite the great advancement made on defluoroborylation of 1-(trifluoromethyl)alkenes, straightforward borylation without fluorine elimination is a blank.…”

Section: Introductionmentioning

confidence: 99%

Cu-Catalyzed Regio- and Stereodivergent Chemoselective sp/sp 1,3- and 1,4-Diborylations of CF3-Containing 1,3-Enynes

Kuang

Chen

Qiu

et al. 2020

Chem

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CF 3 -containing diborylated compounds were successfully prepared from readily available CF 3 bearing 1,3-enynes, without fluorine elimination, and subsequently, several useful fluorine-containing molecules were synthesized. These transformations exhibit a high degree of regio-, stereo-, and chemoselectivity, affording CF 3 containing E-1,3-, Z-1,3and Z-1,4-diborylated olefins. Control experiments and density functional theory calculations provide explanations for the observed selectivities.

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Enantioselective Copper-Catalyzed Defluoroalkylation Using Arylboronate-Activated Alkyl Grignard Reagents

Cited by 144 publications

References 45 publications

Sulfonate N‐Heterocyclic Carbene–Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C−C, C−B, C−H, and C−Si Bonds

Sulfonate N‐Heterocyclic Carbene–Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C−C, C−B, C−H, and C−Si Bonds

Catalytic Enantioselective Allylic C–F Bond Functionalization

Cu-Catalyzed Regio- and Stereodivergent Chemoselective sp/sp 1,3- and 1,4-Diborylations of CF3-Containing 1,3-Enynes

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