Transition‐Metal‐Free Borylation of Alkynes and Alkenes

Deng, Chun M.; F., Yi; Wen, Yong

doi:10.1002/slct.201800038

Cited by 10 publications

(5 citation statements)

References 53 publications

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“…However, this hypothesis has not been proven yet. Another report appeared just a year later, which dealt with NaOMe as an initiator in the syn ‐hydroboration of terminal as well as internal alkynes (Scheme 17b) [81] . Notably, a trace of anti ‐hydroborated product was also obtained during this process.…”

Section: Syn‐hydroboration Of Alkynesmentioning

confidence: 99%

Overview of Regioselective and Stereoselective Catalytic Hydroboration of Alkynes

2021

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Hydroboration of alkynes is of special interest to researchers since it is the most straightforward process for the synthesis of highly important vinylborane synthetic intermediate compounds. It is significant in terms of both regioselectivity and stereoselectivity, since several positional isomers are formed during the process of hydroboration. Given the importance of this class of compounds, an extensive study has been carried out regarding catalytic condition development and detailed mechanistic studies for selectively obtaining a single isomer. This review comprehensively summarizes both the regioselective and stereoselective catalytic hydroboration of alkynes. It is aimed at giving readers accurate knowledge of the catalytic systems available for the hydroboration of certain alkynes. We anticipate that this inclusive review will encourage researchers to explore more new types of catalytic systems to achieve the remarkable process of hydroboration of alkynes.

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Section: Syn‐hydroboration Of Alkynesmentioning

confidence: 99%

Overview of Regioselective and Stereoselective Catalytic Hydroboration of Alkynes

2021

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“…Several research groups have reported the regioselective and stereoselective hydroboration of alkynes and alkenes to produce vinyl boronates and alkyl boronate, catalyzed by transition metals such as Fe, Co, Cu, Ru, Rh, and Ir . Additionally, there are some reports of hydroboration of carbonyl compounds affording boronic esters, catalyzed by Co, Fe, and Ru. − Main-group metal-catalyzed hydroboration of terminal alkynes and organic nitriles is also well reported in the literature. − Using commercially available aluminum hydride ( i Bu 2 AlH) and LiAlH 4 or sodium borohydride (NaBH 4 ) is a well-known means of reduction of alkynes and alkenes, followed by aryl and alkyl nitriles . However, these reagents are combustible and generate large amounts of inorganic waste, which render the process unfavorable.…”

Section: Introductionmentioning

confidence: 99%

Highly Chemoselective Hydroboration of Alkynes and Nitriles Catalyzed by Group 4 Metal Amidophosphine–Borane Complexes

et al. 2020

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We report a series of titanium and zirconium complexes supported by dianionic amidophosphine−borane ligands, synthesized by amine elimination and salt metathesis reactions. The Ti IV complex [{Ph 2 P(BH 3 )N} 2 C 6 H 4 Ti(NMe 2 ) 2 ] (1) was obtained by the reaction between tetrakis-(dimethylamido)titanium(IV) and the protic aminophosphine−borane ligand [{Ph 2 P(BH 3 )NH} 2 C 6 H 4 ] (LH2) at ambient temperature. Both the heteroleptic zirconium complexes[η 5 -(C 5 H 5 ) 2 Zr{Ph 2 P-(BH 3 )N} 2 C 6 H 4 ] (2) and [[{Ph 2 P(BH 3 )N} 2 C 6 H 4 ]ZrCl 2 ] (3)and the homoleptic zirconium complex [[{Ph 2 P(BH 3 )-N} 2 C 6 H 4 ] 2 Zr] (4) were obtained in good yield by the salt metathesis reaction of either zirconocene dichloride [η 5 -(C 5 H 5 ) 2 ZrCl 2 ] or zirconium tetrachloride with the dilithium salt of the ligand [{Ph 2 P(BH 3 )NLi} 2 C 6 H 4 ] ( LLi2), which was prepared in situ. The molecular structures of the complexes 1, 2, and 4 in their solid states were confirmed by single-crystal X-ray diffraction analysis. Of these complexes, only titanium complex 1 acts as an effective catalyst for the facile hydroboration of terminal alkynes, yielding exclusive E-isomers. The hydroboration of organic nitriles yielded diborylamines with a broad substrate scope, including broad functional group compatibility. The mechanism of hydroboration occurs through the formation of titanium hydride as an active species.

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“…Product of single configuration can be obtained by advanced conditions especially rhodium catalytic system [66][67][68]. Hydroboration with diboride will generate 1,2-bis(boronates) [69] which can be further oxidated to vicinal diol (Scheme 6k). The participation of rhodium [70] and platinum [71] catalysts will lead to enantioselective products.…”

Section: Derivatization Strategies Of Phenylpropanoid Fragments 231 C...mentioning

confidence: 99%

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

Ding

Jiang

Zhang

et al. 2022

Nat. Prod. Bioprospect.

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Structural derivatization of natural products has been a continuing and irreplaceable source of novel drug leads. Natural phenols are a broad category of natural products with wide pharmacological activity and have offered plenty of clinical drugs. However, the structural complexity and wide variety of natural phenols leads to the difficulty of structural derivatization. Skeleton analysis indicated most types of natural phenols can be structured by the combination and extension of three common fragments containing phenol, phenylpropanoid and benzoyl. Based on these fragments, the derivatization strategies of natural phenols were unified and comprehensively analyzed in this review. In addition to classical methods, advanced strategies with high selectivity, efficiency and practicality were emphasized. Total synthesis strategies of typical fragments such as stilbenes, chalcones and flavonoids were also covered and analyzed as the supplementary for supporting the diversity-oriented derivatization of natural phenols.

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Transition‐Metal‐Free Borylation of Alkynes and Alkenes

Cited by 10 publications

References 53 publications

Overview of Regioselective and Stereoselective Catalytic Hydroboration of Alkynes

Overview of Regioselective and Stereoselective Catalytic Hydroboration of Alkynes

Highly Chemoselective Hydroboration of Alkynes and Nitriles Catalyzed by Group 4 Metal Amidophosphine–Borane Complexes

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

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