Mild, effective and selective method for the silylation of alcohols using silazanes promoted by catalytic tetrabutylammonium fluoride

Tanabe, Yoo; Murakami, M.; Kitaichi, Kazuto; Yoshida, Yoshitoku

doi:10.1016/s0040-4039(00)74419-4

Cited by 68 publications

(24 citation statements)

References 6 publications

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“…[31] This proved to be successful and a number of different alcohols were tried and the results, together with those from the Pauson-Khand reaction are shown in Table 1.…”

Section: Resultsmentioning

confidence: 99%

The use of silicon-based tethers for the Pauson-Khand reaction

Dobbs¹,

Miller²,

Martinović³

2007

Beilstein J. Org. Chem.

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“…[31] This proved to be successful and a number of different alcohols were tried and the results, together with those from the Pauson-Khand reaction are shown in Table 1.…”

Section: Resultsmentioning

confidence: 99%

The use of silicon-based tethers for the Pauson-Khand reaction

Dobbs¹,

Miller²,

Martinović³

2007

Beilstein J. Org. Chem.

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“…The resulting molecular or macromolecular products have attractive properties as emissive materials, high‐performance elastomers, synthetic precursors for ceramic thin films and monoliths, and for biomedical applications 61. The formation of NSi bonds yields silazanes, and this has become an integral part of our research program in Ae‐catalyzed reactions when we fortuitously became aware that Ae catalysts could catalyze the coupling of primary amines with [Ae]–N(SiMe 2 H) 2 residues (see Section 3.1) Silazanes are valuable ligands in coordination chemistry,62 bases,63 silylating agents,64 or protecting groups for amines, indoles, and anilines 65. Moreover, oligo‐ and polysilazanes are good precursors of Si 3 N 4 ceramics 66.…”

Section: Sih/h–n Dehydrocoupling Catalysismentioning

confidence: 99%

Calcium, Strontium and Barium Homogeneous Catalysts for Fine Chemicals Synthesis

Sarazin

Carpentier

2016

The Chemical Record

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The large alkaline earths (Ae), calcium, strontium and barium, have in the past 15 years yielded a brand new generation of heteroleptic molecular catalysts for the production of fine chemicals. However, the integrity of these complexes is often plagued by ligand redistribution equilibria in solution. This personal account retraces the paths followed in our research group towards the design of stable heteroleptic alkalino-earth complexes, including the use of intramolecular noncovalent Ae···H-Si and Ae···F-C interactions. Their implementation as homogenous precatalysts for reactions such as the intramolecular and intermolecular hydroamination and hydrophosphination of activated alkenes, the hydrophosphonylation of ketones, and the dehydrogenative coupling of amines and hydrosilanes that enable the efficient and controlled formations of CP, CN, or SiN σ-bonds, is presented in a synthetic perspective that highlights their overall outstanding catalytic performance.

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“…18 Silylation of tertiary allylic alcohol 15 with TMS-imidazole and a catalytic amount of tetrabutylammonium fluoride (TBAF) provided the Prins–pinacol precursor 16 in 76% yield. 19 …”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of (+)-Sieboldine A: Evolution of a Pinacol-Terminated Cyclization Strategy

Canham

Overman

2012

J. Org. Chem.

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This article describes synthetic studies that culminated in the first total synthesis of the Lycopodium alkaloid sieboldine A. During this study a number of pinacol-terminated cationic cyclizations were examined to form the cis-hydrindanone core of sieboldine A. Of these, a mild Au(I)-promoted 1,6-enyne cyclization that was terminated by a semipinacol rearrangement proved to be most efficient. Fashioning the unprecedented N-hydroxyazacyclononane ring embedded within the bicyclo[5.2.1]decane-N,O-acetal moiety of sieboldine A was a formidable challenge. Ultimately, the enantioselective total synthesis of (+)-sieboldine A was completed by forming this ring in good yield by cyclization of a protected-hydroxylamine thioglycoside precursor.

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Mild, effective and selective method for the silylation of alcohols using silazanes promoted by catalytic tetrabutylammonium fluoride

Cited by 68 publications

References 6 publications

The use of silicon-based tethers for the Pauson-Khand reaction

The use of silicon-based tethers for the Pauson-Khand reaction

Calcium, Strontium and Barium Homogeneous Catalysts for Fine Chemicals Synthesis

Total Synthesis of (+)-Sieboldine A: Evolution of a Pinacol-Terminated Cyclization Strategy

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