Concepedia

Diels–Alder Reaction of 2,3-Bis(pinacolatoboryl)-1,3-butadiene: Facile Preparation of 1,2-Bis(pinacolatoboryl)cyclohexenes and -1,4-cyclohexadiene

Masaki Shimizu, Katsuhiro Shimono, Takuya Kurahashi, Shin‐ichi Kiyomoto, Ikuhiro Nagao, Tamejiro Hiyama

Bulletin of the Chemical Society of Japan · 2008 · 18 citations · 25 references

DOI

Concepts

Abstract

Abstract Diels–Alder reaction of 2,3-bis(pinacolato)boryl-1,3-butadiene with electron-deficient alkenes and dimethyl acetylenedicarboxylate proceeded smoothly upon heating, giving rise to the corresponding 1,2-diborylcyclohexenes in good to excellent yields. Conversion of two C–B bonds in the cycloadducts into C–C bonds is also demonstrated.

References

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Chemistry of Group 13 element-transition metal linkage — the platinum- and palladium-catalyzed reactions of (alkoxo)diborons

Tatsuo Ishiyama, Norio Miyaura · Journal of Organometallic Chemistry · 2000 · 313 citations · Full text

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Synthesis and Characterization of Platinum(II)−Bis(boryl) Catalyst Precursors for Diboration of Alkynes and Diynes:  Molecular Structures of <i>cis</i>-[(PPh<sub>3</sub>)<sub>2</sub>Pt(B-4-Bu<sup>t</sup>cat)<sub>2</sub>], <i>cis</i>-[(PPh<sub>3</sub>)<sub>2</sub>Pt(Bcat)<sub>2</sub>], <i>cis</i>-[(dppe)Pt(Bcat)<sub>2</sub>], <i>cis</i>-[(dppb)Pt(Bcat)<sub>2</sub>], (<i>E</i>)-(4-MeOC<sub>6</sub>H<sub>4</sub>)C(Bcat)CH(Bcat), (<i>Z</i>)-(C<sub>6</sub>H<sub>5</sub>)C(Bcat)C(C<sub>6</sub>H<sub>5</sub>)(Bcat), and (<i>Z</i>,<i>Z</i>)-(4-MeOC<sub>6</sub>H<sub>4</sub>)C(Bcat)C(Bcat)C(Bcat)C(4-MeOC<sub>6</sub>H<sub>4</sub>)(Bcat) (cat = 1,2-O<sub>2</sub>C<sub>6</sub>H<sub>4</sub>; dppe = Ph<sub>2</sub>PCH<sub>2</sub>CH<sub>2</sub>PPh<sub>2</sub>; dppb = Ph<sub>2</sub>P(CH<sub>2</sub>)<sub>4</sub>PPh<sub>2</sub>)

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