Haloboration of internal alkynes with boronium and borenium cations as a route to tetrasubstituted alkenes

James R. Lawson; Ewan R. Clark; Ian A. Cade; Sophia A. Solomon; Michael J. Ingleson

doi:10.1002/anie.201302609

Haloboration of internal alkynes with boronium and borenium cations as a route to tetrasubstituted alkenes

James R. Lawson, Ewan R. Clark, Ian A. Cade, Sophia A. Solomon, Michael J. Ingleson^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Hail boration! 2-Dimethylaminopyridine-ligated dihaloborocations [X ₂B(2-DMAP)]⁺ with a strained four-membered boracycle were used for the haloboration of terminal and dialkyl internal alkynes (see scheme). Esterification then provided vinyl boronate esters as useful precursors to tetrasubstituted alkenes. Following mechanistic studies, the scope of the haloboration was expanded simply by variation of the amine. Pin=2,3-dimethyl-2, 3-butanedioxy.

Original language	English
Pages (from-to)	7518-7522
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	29
DOIs	https://doi.org/10.1002/anie.201302609
Publication status	Published - 15 Jul 2013

Keywords / Materials (for Non-textual outputs)

borenium ions
boronate esters
haloboration
synthetic methods
tetrasubstituted alkenes

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10.1002/anie.201302609

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title = "Haloboration of internal alkynes with boronium and borenium cations as a route to tetrasubstituted alkenes",

abstract = "Hail boration! 2-Dimethylaminopyridine-ligated dihaloborocations [X 2B(2-DMAP)]+ with a strained four-membered boracycle were used for the haloboration of terminal and dialkyl internal alkynes (see scheme). Esterification then provided vinyl boronate esters as useful precursors to tetrasubstituted alkenes. Following mechanistic studies, the scope of the haloboration was expanded simply by variation of the amine. Pin=2,3-dimethyl-2, 3-butanedioxy.",

keywords = "borenium ions, boronate esters, haloboration, synthetic methods, tetrasubstituted alkenes",

author = "Lawson, {James R.} and Clark, {Ewan R.} and Cade, {Ian A.} and Solomon, {Sophia A.} and Ingleson, {Michael J.}",

year = "2013",

month = jul,

day = "15",

doi = "10.1002/anie.201302609",

language = "English",

volume = "52",

pages = "7518--7522",

journal = "Angewandte Chemie - International Edition",

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T1 - Haloboration of internal alkynes with boronium and borenium cations as a route to tetrasubstituted alkenes

AU - Lawson, James R.

AU - Clark, Ewan R.

AU - Cade, Ian A.

AU - Solomon, Sophia A.

AU - Ingleson, Michael J.

PY - 2013/7/15

Y1 - 2013/7/15

N2 - Hail boration! 2-Dimethylaminopyridine-ligated dihaloborocations [X 2B(2-DMAP)]+ with a strained four-membered boracycle were used for the haloboration of terminal and dialkyl internal alkynes (see scheme). Esterification then provided vinyl boronate esters as useful precursors to tetrasubstituted alkenes. Following mechanistic studies, the scope of the haloboration was expanded simply by variation of the amine. Pin=2,3-dimethyl-2, 3-butanedioxy.

AB - Hail boration! 2-Dimethylaminopyridine-ligated dihaloborocations [X 2B(2-DMAP)]+ with a strained four-membered boracycle were used for the haloboration of terminal and dialkyl internal alkynes (see scheme). Esterification then provided vinyl boronate esters as useful precursors to tetrasubstituted alkenes. Following mechanistic studies, the scope of the haloboration was expanded simply by variation of the amine. Pin=2,3-dimethyl-2, 3-butanedioxy.

KW - borenium ions

KW - boronate esters

KW - haloboration

KW - synthetic methods

KW - tetrasubstituted alkenes

UR - http://www.scopus.com/inward/record.url?scp=84880089639&partnerID=8YFLogxK

U2 - 10.1002/anie.201302609

DO - 10.1002/anie.201302609

M3 - Article

AN - SCOPUS:84880089639

SN - 1433-7851

VL - 52

SP - 7518

EP - 7522

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 29

ER -

Haloboration of internal alkynes with boronium and borenium cations as a route to tetrasubstituted alkenes

Abstract

Keywords / Materials (for Non-textual outputs)

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