god and chemistry
3090
3090▌
SHORT REVIEW
Reaction of Diazo Compounds with Organoboron Compounds short review
Huan Li, Yan Zhang, Jianbo Wang*
Reaction of Diazo Compounds with Organoboron Compounds
Abstract: The transition-metal-free reactions of diazo compounds with organoboron compounds are reviewed. This type of reaction provides an alternative approach for the formation of C–C, C–B, and C–Si bonds. Moreover, by using tosylhydrazones as diazo compound precursors and boronic acids/esters as the boron substrates, this type of reaction becomes of practical use in organic synthesis.
This short review covers the recent developments of this area with an introduction to the historical background.
1
2
3
Introduction
Reaction of Diazo Compounds with Organoboranes
Reactions of Diazo Compounds with Boronic Acids and
Related Organoborons
Reaction of Diazo Compounds with Boronic Esters
Concluding Remarks
4
5
Key words: diazo compounds, boron, hydrazine, transition-metalfree reactions, 1,2-migration
1
Introduction
Diazo compounds are useful building blocks in organic synthesis as a result of their diverse reactivity in various reactions and functional group transformations.1,2 In most cases, diazo compounds are used as the precursors of free carbene or metal carbene species C (Scheme 1). Typical reactions of metal carbenes include X–H insertions
(X = C, N, O, S, etc.), cyclopropanation, ylide reactions,
1,2-migration reactions, and olefin metathesis. Recently, transition-metal-catalyzed cross-coupling reactions with diazo compounds have also attracted attention in organic synthesis.3 B
N2
A
N2
B
X
X
– N2
B
N2
D tetracoordinated boron
B
X
E
MLn
MLn
classic metal carbene transformations
+ coupling reactions
Huan Li received his B.Sc. from Wuhan University (P. R. of China) in 2009. He then joined Prof. Jianbo Wang’s group in Peking University as a Ph.D. graduate student. His current research is on
3090▌
SHORT REVIEW
Reaction of Diazo Compounds with Organoboron Compounds short review
Huan Li, Yan Zhang, Jianbo Wang*
Reaction of Diazo Compounds with Organoboron Compounds
Abstract: The transition-metal-free reactions of diazo compounds with organoboron compounds are reviewed. This type of reaction provides an alternative approach for the formation of C–C, C–B, and C–Si bonds. Moreover, by using tosylhydrazones as diazo compound precursors and boronic acids/esters as the boron substrates, this type of reaction becomes of practical use in organic synthesis.
This short review covers the recent developments of this area with an introduction to the historical background.
1
2
3
Introduction
Reaction of Diazo Compounds with Organoboranes
Reactions of Diazo Compounds with Boronic Acids and
Related Organoborons
Reaction of Diazo Compounds with Boronic Esters
Concluding Remarks
4
5
Key words: diazo compounds, boron, hydrazine, transition-metalfree reactions, 1,2-migration
1
Introduction
Diazo compounds are useful building blocks in organic synthesis as a result of their diverse reactivity in various reactions and functional group transformations.1,2 In most cases, diazo compounds are used as the precursors of free carbene or metal carbene species C (Scheme 1). Typical reactions of metal carbenes include X–H insertions
(X = C, N, O, S, etc.), cyclopropanation, ylide reactions,
1,2-migration reactions, and olefin metathesis. Recently, transition-metal-catalyzed cross-coupling reactions with diazo compounds have also attracted attention in organic synthesis.3 B
N2
A
N2
B
X
X
– N2
B
N2
D tetracoordinated boron
B
X
E
MLn
MLn
classic metal carbene transformations
+ coupling reactions
Huan Li received his B.Sc. from Wuhan University (P. R. of China) in 2009. He then joined Prof. Jianbo Wang’s group in Peking University as a Ph.D. graduate student. His current research is on
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