Hydroxy group-enabled highly regio- and stereo-selective hydrocarboxylation of alkynes

Huang, Chaofan; Qian, Hui; Zhang, Wanli; Ma, Shengming

doi:10.1039/c8sc05743e

Cited by 13 publications

(4 citation statements)

References 53 publications

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“…TYC Reaction via Amide Hydrogen Bond Control. Mal and coworkers overcame the stereoselective issues 45 on the alkyne hydrothiolation reactions of internal alkynes. 46 The oxygen atom in enolizable carbonyls of 7 makes amide nitrogen non-basic.…”

Section: Hydrogen Bonding (H-bonding) As Reaction Controllermentioning

confidence: 99%

Weak Interactions in Carbon-Hetero Atom Bond Forming Reactions

Bose¹,

Mal²

2021

Prayogik Rasayan

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Controlling various reactions by multiple weak interactions or soft forces has become an widespread topic under supramolecular catalysis. This review has made a literature collection that explores cooperative weak or noncovalent interactions. These are charge transfer complexation, H-bonding, S-H…π, acid-base, cation- π, etc., towards C-hetero bond formation reactions. This review article will discuss the specific reactivity of chemical systems controlled by weak interactions.

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Section: Hydrogen Bonding (H-bonding) As Reaction Controllermentioning

confidence: 99%

Weak Interactions in Carbon-Hetero Atom Bond Forming Reactions

Bose¹,

Mal²

2021

Prayogik Rasayan

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“…TYC by Amide H-Bond Control. Mal and co-workers successfully addressed stereoselective issues 61 in alkyne hydrothiolation chemistry on unactivated internal alkynes. Owing to stronger electronegativity of oxygen atom, the enolizable carbonyls in 66 make amide nitrogen nonbasic and N−H bonds avoid H-bonding.…”

Section: Tec By S−h••mentioning

confidence: 99%

Noncovalent Interactions in C–S Bond Formation Reactions

2020

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Organosulfur compounds are omnipresent in many drugs, natural products, and functional materials; therefore, methodologies of C−S bond formation reactions are desirable in synthesis. The recent trend to control many chemical reactions by cooperative multiple weak interactions have emerged as one of the popular topics in supramolecular catalysis. Herein, we have made a collection of literature which utilizes multiple noncovalent interactions like H-bonding, solvent bonding, S−H•••π, C−H•••π, π−π stacking, charge-transfer complexation, etc. toward aryl C−S bondformation reactions.

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“…In fact, only few aminocarbonylations of "simple" unsymmetrical internal alkynes were reported, [7o,s] leading to unsatisfactory regioselectivity (Scheme 1b). Clearly,c arbonylations of unsymmetrical internal alkynes are more demanding because of their low reactivity and the difficulty in achieving high regioselectivity.N otable exceptions include the recent works on hydroformylation and alkoxycarbonylation reported by the groups of Breit, [8a] You [8b] and Ma, [9] respectively.I nt hese studies,r egioselectivity could be controlled by hydrogen bonding interactions between substrates and catalysts,s teric hinderance and/or chelation.…”

Section: Introductionmentioning

confidence: 99%

A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes

et al. 2020

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Ac hemo-, regio-, and stereoselective mono-hydroamidation of (un)symmetrical 1,3-diynes is described. Keyfor the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos.T he synthetic value of this general approach to synthetically useful a-alkynyl-a, b-unsaturated amides is showcased by diversification of several structurally complex molecules and marketed drugs.C ontrol experiments and density-functional theory (M06L-SMD) computations also suggest the crucial role of the substrate in controlling the regioselectivity of unsymmetrical 1,3-diynes.

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Hydroxy group-enabled highly regio- and stereo-selective hydrocarboxylation of alkynes

Abstract: Hydrogen bonding-enabled highly regio- and stereo-selective hydrocarboxylation of alkynes has been successfully developed to afford 3-hydroxy-2(E)-alkenoates with up to 97% yield.

Cited by 13 publications

References 53 publications

Weak Interactions in Carbon-Hetero Atom Bond Forming Reactions

Weak Interactions in Carbon-Hetero Atom Bond Forming Reactions

Noncovalent Interactions in C–S Bond Formation Reactions

A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes

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