Addition reactions of bis(pinacolato)diborane(4) to carbonyl enones and synthesis of (pinacolato)2BCH2B and (pinacolato)2BCH2CH2B by insertion and coupling

Hijazi Abu Ali; Israel Goldberg; Morris Srebnik

doi:10.1021/om010282r

Addition reactions of bis(pinacolato)diborane(4) to carbonyl enones and synthesis of (pinacolato)₂BCH₂B and (pinacolato)₂BCH₂CH₂B by insertion and coupling

Hijazi Abu Ali, Israel Goldberg, Morris Srebnik^*

^*Corresponding author for this work

School of Chemistry

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

Abstract

The title compound adds to αβ-unsaturated carbonyls to give the products of 1,4-addition after hydrolysis of the intermediate boron enolates, in 68-86% isolated yield (four examples). In addition, we discovered that diazomethane reacts with bis(pinacolato)diborane to insert methylene to give (pinacolato)₂BCH₂B in 83% yield. An alternative synthesis involved coupling of (pinacolato)BCH₂I with various metals.

Original language	English
Pages (from-to)	3962-3965
Number of pages	4
Journal	Organometallics
Volume	20
Issue number	18
DOIs	https://doi.org/10.1021/om010282r
State	Published - 3 Sep 2001

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abstract = "The title compound adds to αβ-unsaturated carbonyls to give the products of 1,4-addition after hydrolysis of the intermediate boron enolates, in 68-86% isolated yield (four examples). In addition, we discovered that diazomethane reacts with bis(pinacolato)diborane to insert methylene to give (pinacolato)2BCH2B in 83% yield. An alternative synthesis involved coupling of (pinacolato)BCH2I with various metals.",

author = "Ali, {Hijazi Abu} and Israel Goldberg and Morris Srebnik",

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AU - Goldberg, Israel

AU - Srebnik, Morris

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N2 - The title compound adds to αβ-unsaturated carbonyls to give the products of 1,4-addition after hydrolysis of the intermediate boron enolates, in 68-86% isolated yield (four examples). In addition, we discovered that diazomethane reacts with bis(pinacolato)diborane to insert methylene to give (pinacolato)2BCH2B in 83% yield. An alternative synthesis involved coupling of (pinacolato)BCH2I with various metals.

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Addition reactions of bis(pinacolato)diborane(4) to carbonyl enones and synthesis of (pinacolato)₂BCH₂B and (pinacolato)₂BCH₂CH₂B by insertion and coupling

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