Journal ArticleDOI
A novel reduction of alcohols and ethers with a HSiEt3catalytic B(C6F5)3 system
TLDR
In this paper, the secondary alcohols (1g,h) and tertiary alcohol 1i, as well as tertiary alkyl ether 4i, did not react with the HSiEt 3 ( B(C 6 F 5 ) 3 reducing reagent at all.About:
This article is published in Tetrahedron Letters.The article was published on 1999-12-10. It has received 164 citations till now. The article focuses on the topics: Ether & Silyl ether.read more
Citations
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Journal ArticleDOI
Studies on the Mechanism of B(C6F5)3-Catalyzed Hydrosilation of Carbonyl Functions
TL;DR: This mechanistic proposal is supported by a kinetic isotope effect of 1.4(5) for the hydrosilation of acetophenone, the observation that B(C(6)F(5))(3) catalyzes H/D and H/H scrambling in silanes in the absence of substrate, computational investigations, the synthesis of models for proposed intermediates, and other isotope labeling and crossover experiments.
Journal ArticleDOI
A unified survey of Si–H and H–H bond activation catalysed by electron-deficient boranes
TL;DR: This review comprehensively summarises synthetic methods involving borane-catalysed Si-H and H-H bond activation and systems corresponding to an FLP-type situation are not covered.
Journal ArticleDOI
Zinc-Catalyzed Reduction of Amides: Unprecedented Selectivity and Functional Group Tolerance
TL;DR: A novel zinc-catalyzed reduction of tertiary amides was developed that shows remarkable chemoselectivity and substrate scope tolerating ester, ether, nitro, cyano, azo, and keto substituents.
Journal ArticleDOI
A Novel B(C6F5)3-Catalyzed Reduction of Alcohols and Cleavage of Aryl and Alkyl Ethers with Hydrosilanes†
TL;DR: It was found that the secondary alcohols 1g-i and tertiary alcohol 1j, as well as the tertiary alkyl ether 4l, did not react with HSiEt(3) reducing reagent at all, and the following relative reactivity order of substrates was found: primary >> secondary > tertiary.
Journal ArticleDOI
Highly Efficient B(C6F5)3-Catalyzed Hydrosilylation of Olefins†
TL;DR: The possibility to employ aryl-containing hydrosilanes in this reaction opens broad capabilities for the synthesis of alcohols via a trans- selective hydrosilylation/Tamao-Fleming oxidation sequence, complementary to the existing cis-selective hydroboration/oxidation protocol.
References
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Journal ArticleDOI
B(C6F5)3-Catalyzed Silation of Alcohols: A Mild, General Method for Synthesis of Silyl Ethers
TL;DR: The commercially available borane tris(pentafluorophenyl)borane, B(C(6)F(5))(3), is an effective catalyst for the dehydrogenative silation of alcohols using a variety of silanes, R(3)SiH, R[2]SiH(2), and R(2)R'SiH; the selectivity of the silation reactions are roughly governed by the relative basicity of the alcohols
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Reduction of aldehydes and ketones to alcohols and hydrocarbons through use of the organosilane-boron trifluoride system
James L. Fry,Michael Orfanopoulos,Merwyn G. Adlington,William P. Dittman,Steven B. Silverman +4 more
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Selective Reduction of Diaryl or Aryl Alkyl Alcohols in the Presence of Primary Hydroxyl or Ester Groups by Etherated Boron Trifluoride-Triethylsilane System
TL;DR: In this paper, aryl alkyl carbinols bearing a second reducible functional group (such as hydroxyl or ester) are selectively deoxygenated in high yields by the action of etherated boron trifluoride and triethyl silane reducing system.
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Ionic hydrogenations using boron trifluoride hydrate. Reductions of polycyclic aromatics
John W. Larsen,Laurence W. Chang +1 more
TL;DR: In this article, the boron trifluoride monohydrate and triethylsilane pair were used for hydrogenation of anthracene, naphthacene, phenanthrene, 1-methylnaphthalene, etc.