Organoboranes. 38. A facile and highly efficient addition of B-1-alkynyl-9-borabicyclo[3.3.1]nonanes to aldehydes and ketones: an exceptionally chemoselective synthesis of propargylic alcohols

doi:10.1021/JO00210A003

Journal ArticleDOI

Organoboranes. 38. A facile and highly efficient addition of B-1-alkynyl-9-borabicyclo[3.3.1]nonanes to aldehydes and ketones: an exceptionally chemoselective synthesis of propargylic alcohols

Herbert C. Brown, +3 more

- 01 May 1985 -

Journal of Organic Chemistry

- Vol. 50, Iss: 10, pp 1577-1582

TLDR

Les alcyne-1'yl-9 bora-9bicyclo [4.1.0] nonanes permettent de faire la distinction entre les aldehydes and cetones plus ou moins encombres steriquement.

Abstract:

Les alcyne-1'yl-9 bora-9bicyclo [4.1.0] nonanes permettent de faire la distinction entre les aldehydes et cetones plus ou moins encombres steriquement

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Alkynylboranes in the Suzuki-Miyaura coupling

John A. Soderquist, +3 more

- 03 Apr 1995 -

Tetrahedron Letters

TL;DR: In this article, the Suzuki-Miyaura coupling was used to produce a variety of alkynyl derivatives, including B-methoxy-9-borabicyclo[3.3.1]nonane.

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Journal ArticleDOI

A straightforward, efficient and versatile preparation of propargylic alcohols from 1- alkynes and aldehydes via GaI3 and amine

Ying Han, +1 more

- 02 Oct 1995 -

Tetrahedron Letters

TL;DR: The straightforward addition of 1-alkynes to aldehydes in the presence of GaI 3 and an amine gave propargylic alcohol in moderate to high yields as discussed by the authors.

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Solvent-free synthesis of naphthopyrans under ball-milling conditions

Ya-Wei Dong, +2 more

- 27 Oct 2008 -

Tetrahedron

TL;DR: In this article, the nucleophilic addition reactions of terminal alkynes to carbonyl compounds promoted by KOH proceeded efficiently at ambient temperature under solvent-free ball-milling conditions, and subsequent cyclization reactions of the synthesized propargylic alcohols with 2-naphthol catalyzed by indium trichloride tetrahydrate, leading to the formation of naphthopyrans were investigated.

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Journal ArticleDOI

InBr3-Et3N promoted alkynylation of aldehydes and N, O-acetals under mild conditions: facile and simple preparation of propargylic alcohols and amines

Norio Sakai, +2 more

- 26 May 2003 -

Tetrahedron Letters

TL;DR: In this paper, the use of a novel InBr 3 −Et 3 N reagent system to promote addition reactions of 1-alkynes not only with a variety of aromatic or bulky aliphatic aldehydes but also with N, O -acetals is described.

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Journal ArticleDOI

Alkynylation of carbonyl compounds with terminal acetylenes promoted by ZnCl2 and Et3N: simple, mild and efficient preparation of propargylic alcohols

Biao Jiang, +1 more

- 11 Nov 2002 -

Tetrahedron Letters

TL;DR: In this paper, a mild and efficient addition of terminal acetylenes to carbonyl compounds in the presence of ZnCl 2 and Et 3 N gives propargylic alcohols in good to high yields.

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