Network


Latest external collaboration on country level. Dive into details by clicking on the dots.

Hotspot


Dive into the research topics where Jinghan Gui is active.

Publication


Featured researches published by Jinghan Gui.


Nature | 2014

Functionalized olefin cross-coupling to construct carbon–carbon bonds

Julian C. Lo; Jinghan Gui; Yuki Yabe; Chung-Mao Pan; Phil S. Baran

Carbon–carbon (C–C) bonds form the backbone of many important molecules, including polymers, dyes and pharmaceutical agents. The development of new methods to create these essential connections in a rapid and practical fashion has been the focus of numerous organic chemists. This endeavour relies heavily on the ability to form C–C bonds in the presence of sensitive functional groups and congested structural environments. Here we report a chemical transformation that allows the facile construction of highly substituted and uniquely functionalized C–C bonds. Using a simple iron catalyst, an inexpensive silane and a benign solvent under ambient atmosphere, heteroatom-substituted olefins are easily reacted with electron-deficient olefins to create molecular architectures that were previously difficult or impossible to access. More than 60 examples are presented with a wide array of substrates, demonstrating the chemoselectivity and mildness of this simple reaction.


Science | 2015

Practical olefin hydroamination with nitroarenes

Jinghan Gui; Chung-Mao Pan; Ying Jin; Tian Qin; Julian C. Lo; Bryan J. Lee; Steven H. Spergel; Michael E Mertzman; William J. Pitts; Thomas E. La Cruz; Michael A. Schmidt; Nitin Darvatkar; Swaminathan Natarajan; Phil S. Baran

Stitching C-N bonds from nitro groups Numerous compounds in pharmaceutical research have carbon-nitrogen bonds, and chemists are always looking for ways to make them more efficiently. Gui et al. present a method that links the carbon in an olefin to the nitrogen in a nitroaromatic compound (see the Perspective by Kürti). Nitroaromatics are readily available, and the method tolerates a wide range of other chemical groups present on either reacting partner. Science, this issue p. 886; see also p. 863 A method to form carbon-nitrogen bonds via nitro group reduction could streamline synthetic routes in medicinal chemistry. [Also see Perspective by Kürti] The synthesis and functionalization of amines are fundamentally important in a vast range of chemical contexts. We present an amine synthesis that repurposes two simple feedstock building blocks: olefins and nitro(hetero)arenes. Using readily available reactants in an operationally simple procedure, the protocol smoothly yields secondary amines in a formal olefin hydroamination. Because of the presumed radical nature of the process, hindered amines can easily be accessed in a highly chemoselective transformation. A screen of more than 100 substrate combinations showcases tolerance of numerous unprotected functional groups such as alcohols, amines, and even boronic acids. This process is orthogonal to other aryl amine syntheses, such as the Buchwald-Hartwig, Ullmann, and classical amine-carbonyl reductive aminations, as it tolerates aryl halides and carbonyl compounds.


Journal of the American Chemical Society | 2014

C–H Methylation of Heteroarenes Inspired by Radical SAM Methyl Transferase

Jinghan Gui; Qianghui Zhou; Chung-Mao Pan; Yuki Yabe; Aaron C. Burns; Michael Raymond Collins; Martha Ornelas; Yoshihiro Ishihara; Phil S. Baran

A practical C–H functionalization method for the methylation of heteroarenes is presented. Inspiration from Nature’s methylating agent, S-adenosylmethionine (SAM), allowed for the design and development of zinc bis(phenylsulfonylmethanesulfinate), or PSMS. The action of PSMS on a heteroarene generates a (phenylsulfonyl)methylated intermediate that can be easily separated from unreacted starting material. This intermediate can then be desulfonylated to the methylated product or elaborated to a deuteriomethylated product, and can divergently access medicinally important motifs. This mild, operationally simple protocol that can be conducted in open air at room temperature is compatible with sensitive functional groups for the late-stage functionalization of pharmacologically relevant substrates.


Journal of the American Chemical Society | 2017

Fe-Catalyzed C–C Bond Construction from Olefins via Radicals

Julian C. Lo; Dongyoung Kim; Chung-Mao Pan; Jacob T. Edwards; Yuki Yabe; Jinghan Gui; Tian Qin; Sara Gutiérrez; Jessica Giacoboni; Myles W. Smith; Patrick L. Holland; Phil S. Baran

This Article details the development of the iron-catalyzed conversion of olefins to radicals and their subsequent use in the construction of C–C bonds. Optimization of a reductive diene cyclization led to the development of an intermolecular cross-coupling of electronically-differentiated donor and acceptor olefins. Although the substitution on the donor olefins was initially limited to alkyl and aryl groups, additional efforts culminated in the expansion of the scope of the substitution to various heteroatom-based functionalities, providing a unified olefin reactivity. A vinyl sulfone acceptor olefin was developed, which allowed for the efficient synthesis of sulfone adducts that could be used as branch points for further diversification. Moreover, this reactivity was extended into an olefin-based Minisci reaction to functionalize heterocyclic scaffolds. Finally, mechanistic studies resulted in a more thorough understanding of the reaction, giving rise to the development of a more efficient second-generation set of olefin cross-coupling conditions.


Organic Letters | 2013

Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity

Jinghan Gui; Hailong Tian; Weisheng Tian

The first chemical synthesis of glaucogenin D, a 13,14:14,15-disecopregnane steroid with potential antiviral activity, has been accomplished in 12 steps from a hirundigenin-type intermediate. The present route would also be amenable to the synthesis of natural and unnatural glaucogenin derivatives for SAR studies.


Journal of the American Chemical Society | 2018

Scalable Synthesis of Cyclocitrinol

Yu Wang; Wei Ju; Hailong Tian; Weisheng Tian; Jinghan Gui

A 10-step synthesis of the C25 steroid natural product cyclocitrinol from inexpensive, commercially available pregnenolone is reported. This synthesis features a biomimetic cascade rearrangement to efficiently construct the challenging bicyclo[4.4.1] A/B ring system, which enabled a gram-scale synthesis of the bicyclo[4.4.1] enone intermediate 18 in only nine steps. This work also provides experimental support for the biosynthetic origin of cyclocitrinol.


Angewandte Chemie | 2018

Alkynes From Furans: A General Fragmentation Method Applied to the Synthesis of the Proposed Structure of Aglatomin B

Jiachen Deng; Jingjing Wu; Hailong Tian; Jiajing Bao; Yong Shi; Weisheng Tian; Jinghan Gui

Furans are versatile synthons in organic chemistry. Described is a general method for transforming furans into alkynes by dual C-C double-bond cleavage. The reaction is proposed to proceed by sequential [4+2] cycloaddition between furan and singlet oxygen and a formal retro-(3+2) fragmentation of the endoperoxide intermediate. A wide array of furans, including those derived from sapogenins, are amenable to this reaction, thus providing the corresponding alkynoic acids in up to 88 % yields. The synthetic utility was demonstrated by a seven-step synthesis of the proposed structure of a pregnane natural product, aglatomin B, from a known intermediate.


Journal of the American Chemical Society | 2013

Bioconjugation by Native Chemical Tagging of C–H Bonds

Qianghui Zhou; Jinghan Gui; Chung-Mao Pan; Earl Albone; Xin Cheng; Edward M. Suh; Luigi Grasso; Yoshihiro Ishihara; Phil S. Baran


Angewandte Chemie | 2011

Biomimetic Synthesis of 5,6-dihydro-glaucogenin C: Construction of the Disecopregnane Skeleton by Iron(II)-Promoted Fragmentation of an α-Alkoxy Hydroperoxide

Jinghan Gui; Dahai Wang; Weisheng Tian


Tetrahedron Letters | 2012

Stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene through Suzuki–Miyaura cross-coupling

Shunji Zhang; Huaide Dong; Jinghan Gui; Weisheng Tian

Collaboration


Dive into the Jinghan Gui's collaboration.

Top Co-Authors

Avatar

Weisheng Tian

Chinese Academy of Sciences

View shared research outputs
Top Co-Authors

Avatar

Chung-Mao Pan

Scripps Research Institute

View shared research outputs
Top Co-Authors

Avatar

Phil S. Baran

Scripps Research Institute

View shared research outputs
Top Co-Authors

Avatar

Hailong Tian

Chinese Academy of Sciences

View shared research outputs
Top Co-Authors

Avatar

Julian C. Lo

Scripps Research Institute

View shared research outputs
Top Co-Authors

Avatar

Yuki Yabe

Scripps Research Institute

View shared research outputs
Top Co-Authors

Avatar

Tian Qin

Scripps Research Institute

View shared research outputs
Top Co-Authors

Avatar
Top Co-Authors

Avatar
Top Co-Authors

Avatar

Aaron C. Burns

Scripps Research Institute

View shared research outputs
Researchain Logo
Decentralizing Knowledge