The Synthesis of Indoline and Benzofuran Scaffolds Using a Suzuki–Miyaura Coupling/Oxidative Cyclization Strategy

Jana, Somnath; Rainier, Jon D.

doi:10.1021/ol401974v

Cited by 39 publications

(28 citation statements)

References 32 publications

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“…Another interesting approach to obtaining 2‐ C ‐branched glucal derivative 36 has been developed by Jana and Rainier 19. Suzuki–Miyaura coupling between 2‐iodoglucal 20 and (2‐aminophenyl)pinacolborane 35 afforded the aryl compound 36 in good yield (Scheme ).…”

Section: 2‐c‐branched Carbohydratesmentioning

confidence: 99%

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Recent Developments in the Synthesis of 2‐C‐Branched and 1,2‐Annulated Carbohydrates

Vankar

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2015

Eur J Org Chem

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The importance of carbohydrate chemistry in biological and medicinal chemistry has led to enormous developments in the synthesis of carbohydrate mimics. In this context, the synthesis of branched sugars in general and of 2‐C‐branched carbohydrates in particular, as well as the synthesis of 1,2‐annulated sugars, have received immense attention. They serve not only as carbohydrate mimics in the form of stand‐alone molecules, but also as useful intermediates in the synthesis of many natural products, their analogues, and glycosidase inhibitors. This microreview covers the recent synthetic efforts in this area and puts the subject matter into proper perspective for future developments.

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Section: 2‐c‐branched Carbohydratesmentioning

confidence: 99%

“…An interesting example of N ‐cyclization to the anomeric center has been described by Jana and Rainier 19. Aniline derivative 36 , easily available by Suzuki–Miyaura coupling from 2‐iodoglucal 20 (see Scheme ), has been cyclized under two different sets of conditions.…”

Section: 12‐annulated Carbohydratesmentioning

confidence: 99%

Recent Developments in the Synthesis of 2‐C‐Branched and 1,2‐Annulated Carbohydrates

Vankar

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2015

Eur J Org Chem

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“…As a first demonstration of its use in palladium‐catalyzed cross‐coupling reactions, compound 3 f was reacted with phenylacetylene under Pasqua's conditions to generate the corresponding Sonogashira product 10 in good yield. When submitted to a Suzuki‐Miyaura cross‐coupling reaction with phenyl boronic acid under Jana's conditions, 3 f afforded the arylated product 11 in fair yield. Arylation of 3 f through palladium cross‐coupling with triphenylbismuthine using modified Rao's conditions afforded the same product with a similar yield.…”

Section: Introductionmentioning

confidence: 99%

Copper‐Catalyzed β‐Iodovinylation of Carbamates: Expedient Access to Highly Functionalized Vinyl‐Carbamates

2018

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A general and efficient method for the synthesis of β‐iodovinyl carbamates via copper‐catalyzed β‐iodovinylation of acyclic carbamates is described. This method uses readily available (E)‐1,2‐vinyl diiodides and regioselectively affords the corresponding β‐iodovinyl carbamates in good yields with complete stereocontrol of the alkene. Further functionalization of these versatile products leads to a wide diversity of β‐functionalized vinyl‐carbamates in good to excellent yields.

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“…The synthesized 2-C-aryl glycals were next transformed into 1,2-disubstituted sugars by epoxidation of 53 followed by ring-opening with different alcohols under acidic medium which results the desired product 54 in good yields (85-90%). The reduction of glycals double bond gives 1-deoxy sugar 55 in a mixture of diastereoisomers (Scheme 6) Somnath Jana and Jon D. Rainier [20] further utilized the 2-iodo glycals for the synthesis of indoline and benzofuran by using Suzuki-Miyaura cross-coupling approach (Scheme 7). Initially, the reaction of 2-iodo-tri-O-benzyl-D-galactal 56 with 2amino-phenyl boronic acid 57 under palladium catalysis gave the 2-C-arylated glycal in good yield.…”

Section: Synthesis and Transformation Of 2-c-aryl Glycalsmentioning

confidence: 99%

2‐Halo Glycals as “Synthon” for 2‐C‐Branched Sugar: Recent Advances and Applications in Organic Synthesis

2020

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Glycals are unsaturated sugars having an enolic double bond present inside the ring and act as a versatile synthon for the synthesis of natural products and biologically important molecules. The lone pair of endocyclic ring oxygen which is in conjugation with the enolic double bond alters the reactivity of both unsaturated carbons of glycals and directs the selectivity of the incoming group at a particular center. Since the enolic double bond is very much prone to undergo various types of reactions such as epoxidation, addition, formylation, nitration halogenation, etc.; and such type of activated glycals or the derivatives of glycal have been extensively utilized as a precursor for the synthesis of branched sugars. 2-haloglycals have emerged as an important building block for the functionalization at C-2 position of glycals via metal-catalyzed cross-coupling reactions such as Heck, Suzuki, Sonogashira and carbonylative cross-coupling reactions. In this review, we have summarized the recent progress on the utilization of 2-haloglycals for the synthesis of 2-C-branched sugars and further transformation of branched sugars into annulated sugars, heterocycles, and glycoconjugates.[a] Dr.

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The Synthesis of Indoline and Benzofuran Scaffolds Using a Suzuki–Miyaura Coupling/Oxidative Cyclization Strategy

Abstract: The generation of indolines and benzofurans from the combination of Suzuki-Miyaura coupling reactions with oxidative cyclizations is described.

Cited by 39 publications

References 32 publications

Recent Developments in the Synthesis of 2‐C‐Branched and 1,2‐Annulated Carbohydrates

Recent Developments in the Synthesis of 2‐C‐Branched and 1,2‐Annulated Carbohydrates

Copper‐Catalyzed β‐Iodovinylation of Carbamates: Expedient Access to Highly Functionalized Vinyl‐Carbamates

2‐Halo Glycals as “Synthon” for 2‐C‐Branched Sugar: Recent Advances and Applications in Organic Synthesis

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