Synthesis of 2,3-dihydro-1H-phosphindole-1-oxides via the t-BuLi-mediated rearrangement of vinyl bromides and phosphine oxides

Li, Bin; Zhang, Mingkai; Huang, Xu‐Lun; Gu, Zhenhua

doi:10.1039/c7qo00310b

Cited by 5 publications

(1 citation statement)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A series of intermediates for P -ligands were synthesized by the reaction of aryl triflates and diaryl phosphine oxides using Pd 2 (dba) 3 (Scheme 10 ) [ 130 - 136 ]. The selective transformation of the triflate group of 2-bromophenyl trifluoromethanesulfonate [ 130 ], 2-bromo-4-methoxyphenyl trifluoromethanesulphonate [ 131 ] and 1-bromonaphthalen-2-yl trifluoromethanesulfonates [ 132 - 134 ] could be achieved in the presence of a dppp ligand and Hünig- base in toluene. (1-(Naphtho [ 2 ,3-b]furan-9-yl)naphthalen-2-yl)diaryl-phosphine oxides were obtained by similar cross-coupling reactions employing dppb as the ligand and DMSO as the solvent [ 135 ].…”

Section: The Traditional Hirao Reactionmentioning

confidence: 99%

New Developments on the Hirao Reactions, Especially from “Green” Point of View

Henyecz

Keglevich

2019

COS

View full text Add to dashboard Cite

Background: The Hirao reaction discovered ca. 35 years ago is an important P–C coupling protocol between dialkyl phosphites and aryl halides in the presence of Pd(PPh3)4 as the catalyst and a base to provide aryl phosphonates. Then, the reaction was extended to other Preagents, such as secondary phosphine oxides and H-phosphinates and to other aryl and hetaryl derivatives to afford also phosphinic esters and tertiary phosphine oxides. Instead of the Pd(PPh3)4 catalyst, Pd(OAc)2 and Ni-salts were also applied as catalyst precursors together with a number of mono- and bidentate P-ligands. Objective: In our review, we undertook to summarize the target reaction with a special stress on the developments attained in the last 6 years, hence this paper is an update of our earlier reviews in a similar topic. Conclusion: “Greener” syntheses aimed at utilizing phase transfer catalytic and microwave-assisted approaches, even under “P-ligand-free. or even solvent-free conditions are the up-to date versions of the classical Hirao reaction. The mechanism of the reaction is also in the focus these days.

show abstract

Section: The Traditional Hirao Reactionmentioning

confidence: 99%

New Developments on the Hirao Reactions, Especially from “Green” Point of View

Henyecz

Keglevich

2019

COS

View full text Add to dashboard Cite

show abstract

Advancement in Synthetic Strategies of Phosphorus Heterocycles: Recent Progress from Synthesis to Emerging Class of Optoelectronic Materials

Thakur,

Sushmita,

Meena

et al. 2024

The Chemical Record

View full text Add to dashboard Cite

Organophosphorus heterocycles have long been acknowledged for their significant potential across diverse fields, including catalysis, material science, and drug development. Incorporating phosphorus functionalities into organic compounds offers a means to effectively tailor their medicinal properties, augment biological responses, and enhance selectivity and bioavailability. The distinctive physical and photoelectric characteristics of phosphorus‐containing conjugated compounds have garnered considerable interest as promising materials for organic optoelectronics. These compounds find extensive utility in various applications such as light‐emitting diodes, photovoltaic cells, phosphole‐based fluorophores, and semiconductors.

show abstract