Di(isopropylprenyl)borane: A New Hydroboration Reagent for the Synthesis of Alkyl and Alkenyl Boronic Acids

Калинин, А. В.; Scherer, Stefan; Snieckus, Victor

doi:10.1002/anie.200351312

Cited by 61 publications

(35 citation statements)

References 101 publications

(23 reference statements)

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“…Amine 2 was then subjected to a Snieckus hydroboration 8. The resulting boronic acid was quenched with potassium hydrogen fluoride to access the corresponding potassium alkenyltrifluoroborate 3 as a waxy solid.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of the stereogenic triad of the halicyclamine A core

Molander¹,

Cadoret²

2011

Tetrahedron Letters

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We describe herein our progress toward the synthesis of halicyclamine A, which possesses very interesting biological activities and has never been synthesized. For this purpose, we proposed a stereoselective Diels-Alder reaction as a key step for the establishment of the stereogenic triad of the bis(piperidinyl) core of this molecule. A series of NMR studies was then conducted to establish the correct stereochemical assignment subsequent to the Diels-Alder reaction.

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Section: Resultsmentioning

confidence: 99%

Synthesis of the stereogenic triad of the halicyclamine A core

Molander¹,

Cadoret²

2011

Tetrahedron Letters

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“…Several potassium β-aminoethyltrifluoroborates have been prepared through the hydroboration of Nvinyl substrates with di(isopropylprenyl)borane (i-PP 2 BH) followed by treatment with KHF 2 [29], giving rise to aminoethylating reagents [30]. These regents were initially cross-coupled with a variety of aryl and heteroaryl bromides in good yields in the presence of PdCl 2 (dppf) • CH 2 Cl 2 (Scheme 16) [31].…”

Section: Cross-coupling Of Novel Organotrifluoroboratesmentioning

confidence: 99%

Improving Transformations Through Organotrifluoroborates

Traister

Molander

2015

Synthesis and Application of Organoboron Compounds

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“…Substrates 22, with both electron-donating and electron-withdrawing groups on the phenyl ring, performed well in b-borylation reaction giving 88-92 % yield of pure anti-Markovnikov products 23, which are characteristic for uncatalyzed hydroborations. [27,28] (Table 8). It was observed that in this case P^P ligands enabled lower loadings and higher efficiency than monodentate phosphines like Ph 3 P. Surprisingly, a-methylstyrene and b-methylstyrene did not react under similar reaction conditions.…”

Section: Entrymentioning

confidence: 99%

“…In recent years new catalytic systems have evolved to address regioselectivity and enantioselectivity, common challenges of catalytic hydroboration, as well as issues associated with side reactions such as dehydrogenative borylation and alkene hydrogenation. [27,28] Nevertheless, the need of the substrate scope expansion from simple alkenes to electron deficient conjugated analogues triggered further developments in the field. This challenge was first addressed by Marder et al [29] who latter on discovered a transition metal catalyzed addition of diboron reagents [30] to vinylarenes and a,bunsaturated olefins.…”

mentioning

confidence: 99%

Cu^II and Cu⁰ Catalyzed Mono Borylation of Unsaturated Hydrocarbons with B₂pin₂: Entering into the Water

Stavber¹,

Časar

2014

ChemCatChem

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CHEMCATCHEM MINIREVIEWS tions of boron precursors to unsaturated organic frameworks is becoming increasingly popular. The above mentioned drawbacks of organoborane preparation were overcome after the pioneering discovery of Brown, related to the hydroboration of unsaturated organic compounds, in the middle of the previous century. [25] Moreover, Brown and co-workers achieved unprecedented chiral inductions in classical organic synthesis soon after, by employing chiral hydroborating agents. [26] This methodology continues to attract interest, consequently, many transition metal catalyzed approaches have been developed, which allow different regioselectivity than the uncatalyzed hydroborations. In recent years new catalytic systems have evolved to address regioselectivity and enantioselectivity, common challenges of catalytic hydroboration, as well as issues associated with side reactions such as dehydrogenative borylation and alkene hydrogenation. [27,28] Nevertheless, the need of the substrate scope expansion from simple alkenes to electron deficient conjugated analogues triggered further developments in the field. This challenge was first addressed by Marder et al. [29] who latter on discovered a transition metal catalyzed addition of diboron reagents [30] to vinylarenes and a,bunsaturated olefins. [31] Interestingly, the Pt-catalyzed reaction with diboron reagent on Michael acceptors proceeded as 1,4addition giving the unique b-boryl carbonyl compounds. [31b-c, 32] In contrast, catalytic or uncatalyzed hydroboration with HB(cat) or 9-borabicyclononane provided instead the boron enolate products, which upon treatment with different electrophiles afforded alternative products. [33] The scope of metal catalysts capable of b-borylation of a,b-unsaturated olefins was subsequently extended [34] to Ag, [35] Ni, [36] Zn, [37] Pd, [38] Fe, [39] and Cu I . Furthermore, some examples of transition metal free b-borylations with diboron reagents have also been developed recently (Scheme 2). [40] Notably, among metal catalyzed approaches, Cu I based catalysts appear to be the most widely explored, owing to its alluring cost advantage and solid performance over wide variety of substrates. The story of Cu I -catalyzed b-borylations has begun with concomitant discoveries of Hosomi et al. [41] and Miyaura et al. [42] who reported racemic conjugate additions of B 2 pin 2 to a,b-enones. A stunning progress has been made later on in the direction of asymmetric conjugate b-borylation by groups of Yun, [43] Hoveyda, [44] Fernµndez [45] and others [46] who developed catalytic systems based on Cu I -salts and other transition metals, which enabled the creation of stereogenic centers containing CÀB bond in high efficiency and stereoselectivity (Scheme 2). Importantly, Cu I -catalysis was also successfully used in borylation of alkynes. [47] Nevertheless, the transition metal catalyzed b-borylations must be performed in anhydrous organic solvents. Moreover, Cu I -catalyzed procedures require presence of a strong base and alcohol as p...

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Di(isopropylprenyl)borane: A New Hydroboration Reagent for the Synthesis of Alkyl and Alkenyl Boronic Acids

Cited by 61 publications

References 101 publications

Synthesis of the stereogenic triad of the halicyclamine A core

Synthesis of the stereogenic triad of the halicyclamine A core

Improving Transformations Through Organotrifluoroborates

Cu^II and Cu⁰ Catalyzed Mono Borylation of Unsaturated Hydrocarbons with B₂pin₂: Entering into the Water

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Di(isopropylprenyl)borane: A New Hydroboration Reagent for the Synthesis of Alkyl and Alkenyl Boronic Acids

Cited by 61 publications

References 101 publications

Synthesis of the stereogenic triad of the halicyclamine A core

Synthesis of the stereogenic triad of the halicyclamine A core

Improving Transformations Through Organotrifluoroborates

CuII and Cu0 Catalyzed Mono Borylation of Unsaturated Hydrocarbons with B2pin2: Entering into the Water

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Cu^II and Cu⁰ Catalyzed Mono Borylation of Unsaturated Hydrocarbons with B₂pin₂: Entering into the Water