1,1-Carboboration Route to Substituted Naphthalenes

Liedtke, René; Harhausen, Marcel; Fröhlich, Roland; Kehr, Gerald; Erker, Gerhard

doi:10.1021/ol300193e

Cited by 44 publications

(22 citation statements)

References 42 publications

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“…The entire process proceeds easily with high yields (Scheme 22a). 59 The reaction scope can be further enhanced using heterocyclic bis-silylacetylenes resulting in the corresponding carbazoles, benzothiophenes, and quinolones. 60 Curran and co-workers developed a method for bissilylacetylene hydroboration reactions with N-heterocyclic carbene-borane that involves a 1,2-silyl migration (Scheme 22b).…”

Section: Scheme 21 Synthesis Of Stable Gold Complex From Propargylsilmentioning

confidence: 99%

Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift

Beļaunieks

Puriņš²,

Turks³

2020

Synthesis

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Many chemical transformations of organosilicon compounds proceed due to the capability of silyl substituents to stabilize a positive charge in its β-position. This short review provides an overview of the present understanding of the β-silicon effect and focusses on the synthetic applications of 1,2-silyl shifts resulting from non-vertical stabilization of alkylcarbenium ions and vinyl cations. The reactions of silicon containing unsaturated starting materials, alkenes, allenes, and alkynes, involving β-silyl group stabilized cationic intermediates, transition metal carbenes, or vinylidene complexes will be discussed.1 Introduction2 Origins of the β-Silicon Effect3 Reactions of Allenylsilanes4 Reactions of Alkynes4.1 Propargylsilanes4.2 Alkynylsilanes5 Reactions of Alkenes5.1 Allylsilanes5.2 Vinylsilanes6 Conclusions

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Section: Scheme 21 Synthesis Of Stable Gold Complex From Propargylsilmentioning

confidence: 99%

Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift

Beļaunieks

Puriņš²,

Turks³

2020

Synthesis

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“…[33] The reactiono fb orylative cyclization of cylohexadienone con-taininga1,6-enyne fragment, over ac hiralc atalyst, might be effectively used to synthesize enantioselectively-enriched cisdihydrobenzofurane. [34] Organoboron reagents with ap entafluorophenyl substituent in itsb ackbone are widely used for example, as Lewis acids, activatorsi nh omogeneous reaction of Ziegler-Natta catalyst, [35][36][37][38] hydrosilylation, [39][40][41][42][43][44][45][46][47][48] hydroalumination, [49] hydrogermylation as acids, [50][51][52][53][54][55][56][57][58][59][60][61] Lewis chemistry frustrated Lewis pairs (FLP), [55,[62][63][64][65][66][67][68][69] and the reactions of 1,1-carboboration.…”

Section: Organoboration (Carboboration)ofa Lkynesmentioning

confidence: 99%

Recent Advances in Boron‐Substituted 1,3‐Dienes Chemistry: Synthesis and Application

Pyziak

Walkowiak

Marciniec

2016

Chemistry A European J

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In the syntheses developed to access naturally occurring compounds, especially bioactive substances, boron-functionalized dienes (also "linchpin" reagents) are used as key reagents. Structurally unique dienes are found in nature, and play important biological and chemical roles. Recently, linchpin moieties have been proved as useful substrates for a variety of highly functionalized chemical transformations. The products of these processes are potentially of some use for the syntheses of an important class of natural products showing a wide range of biological activities. This review describes progress in the synthesis of borylsubstituted buta-1,3-dienes as well as their application in organic chemistry.

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“…The starting point of this project was the preparation of a library of electrophilic boron compounds that are by nature Lewis acidic but also contain a “transferable” R‐group (Scheme ) . To maintain high Lewis acidity at boron, which is important in the propargyl rearrangement, compounds of the type RB(C 6 F 5 ) 2 and borocations were selected as target boron Lewis acids.…”

Section: Resultsmentioning

confidence: 99%

The Propargyl Rearrangement to Functionalised Allyl‐Boron and Borocation Compounds

Wilkins

Lawson

Wieneke

et al. 2016

Chemistry A European J

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A diverse range of Lewis acidic alkyl, vinyl and aryl boranes and borenium compounds that are capable of new carbon-carbon bond formation through selective migratory group transfer have been synthesised. Utilising a series of heteroleptic boranes [PhB(C6 F5 )2 (1), PhCH2 CH2 B(C6 F5 )2 (2), and E-B(C6 F5 )2 (C6 F5 )C=C(I)R (R=Ph 3 a, nBu 3 b)] and borenium cations [phenylquinolatoborenium cation ([QOBPh][AlCl4 ], 4)], it has been shown that these boron-based compounds are capable of producing novel allyl- boron and boronium compounds through complex rearrangement reactions with various propargyl esters and carbamates. These reactions yield highly functionalised, synthetically useful boron substituted organic compounds with substantial molecular complexity in a one-pot reaction.

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1,1-Carboboration Route to Substituted Naphthalenes

Abstract: 1,2-Bis(alkynyl)benzene derivatives react with strongly electrophilic boranes to yield in boryl-functionalized bulky naphthalene derivatives by means of a sequence of 1,1-carboboration reactions. These substrates can be functionalized by transition metal catalyzed cross-coupling reactions.

Cited by 44 publications

References 42 publications

Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift

Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift

Recent Advances in Boron‐Substituted 1,3‐Dienes Chemistry: Synthesis and Application

The Propargyl Rearrangement to Functionalised Allyl‐Boron and Borocation Compounds

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