Tandem β-boration/arylation of α,β-unsaturated carbonyl compounds by using a single palladium complex to catalyse both steps

Bonet A.; Gulyás H.; Koshevoy I.O.; Estevan F.; Sanaú M.; ?beda M.A.; Fernández E.

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Tandem β-boration/arylation of α,β-unsaturated carbonyl compounds by using a single palladium complex to catalyse both steps

机译：使用单个钯配合物催化两个步骤，对α，β-不饱和羰基化合物进行串联β-硼酸酯化/芳基化

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Diphenyl(3-methyl-2-indolyl)phosphine (C_9H_8NPPh _2, 1) gives stable dimeric palladium(II) complexes that contain the phosphine in P,Nbridging coordination mode. On treating 1 with [Pd(O _2CCH_3)_2], the new complexes [Pd(μ-C _9H_7NPPh_2)-(NCCH_3)]_2 (2) or [Pd(μ-C_9H_7NPPh_2)-(μ-O _2CCH_3)]_2 (3) were isolated, depending on the solvent used, acetonitrile or toluene, respectively. Further reaction of 3 with the ammonium salt of 1 led to the substitution of one carboxylate ligand to afford [Pd(u-C_9H_7NPPh_2)_3(μ-O _2CCH_3)] (4), in which the bimetallic unit is bonded by three C_9H_7NPPh_2~- moieties and one carboxylate group. Using this methodology, [Pd_2(μ-C _6H_4PPh_2)_2(μ-C_9H _7NPPh_2)(μ-O_2CCX_3)] (X = H (7); J. = F (8)) were synthesised from the ortho-metalated compounds [Pd(C _6H_4PPh_2)(μO_2CCX3)], (X = H (5); J. = F (6)). Complexes 3, 4, 7, and 8 have been found to be active in the catalytic β-boration of α,β-unsaturated esters and ketones under mild reaction conditions. Hindrance of the carbonyl moiety has an influence on the reaction rate, but quantitative conversion was achieved in many cases. More remarkably, when aryl bromides were added to the reaction media, complex 7 induced a highly successful consecutive β-boration/crosscoupling reaction with dimethyl acrylamide as the substrate (99% conversion, 89 % isolated yield).

机译：二苯基（3-甲基-2-吲哚基）膦（C_9H_8NPPh _2，1）提供了稳定的二聚钯（II）配合物，该配合物在P，Nbridging配位模式下包含膦。在用[Pd（O _2CCH_3）_2]处理1时，新的络合物[Pd（μ-C_9H_7NPPh_2）-（NCCH_3）] _ 2（2）或[Pd（μ-C_9H_7NPPh_2）-（μ-O_2CCH_3）] _ 2分离（3），具体取决于所使用的溶剂，乙腈或甲苯。 3与1的铵盐的进一步反应导致一个羧酸盐配体的取代，从而产生[Pd（u-C_9H_7NPPh_2）_3（μ-O_2CCH_3）]（4），其中双金属单元通过三个C_9H_7NPPh_2〜键连接-部分和一个羧酸根基团。使用这种方法，[Pd_2（μ-C_6H_4PPh_2）_2（μ-C_9H_7NPPh_2）（μ-O_2CCX_3）]（X = H（7）; J. = F（8））由邻金属化化合物合成[ Pd（C _6H_4PPh_2）（μO_2CCX3）]，（X = H（5）; J. = F（6））。已经发现在温和的反应条件下，配合物3、4、7和8在α，β-不饱和酯和酮的催化β-硼化中具有活性。羰基部分的阻碍对反应速率有影响，但是在许多情况下实现了定量转化。更显着地，当将芳基溴化物添加到反应介质中时，配合物7诱导了以二甲基丙烯酰胺为底物的非常成功的连续β-硼化/交叉偶联反应（99％转化率，89％分离产率）。

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《Chemistry: A European journal》 |2010年第21期|共9页
作者
Bonet A.; Gulyás H.; Koshevoy I.O.; Estevan F.; Sanaú M.; ?beda M.A.; Fernández E.;
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正文语种 eng
中图分类应用化学;
关键词
Arylation; Domino reactions; Heterogeneous catalysism; N; P ligands; Palladium;

机译：芳基化;多米诺反应;非均相催化;N;P配体;钯;

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1. Tandem β-boration/arylation of α,β-unsaturated carbonyl compounds by using a single palladium complex to catalyse both steps [J] . Bonet A., Gulyás H., Koshevoy I.O., Chemistry: A European journal . 2010,第21期

机译：使用单个钯配合物催化两个步骤，对α，β-不饱和羰基化合物进行串联β-硼酸酯化/芳基化
2. Palladium-Catalyzed Heck Reaction on 1-Alkoxy-1,3-dienes: A Regioselective γ-Arylation of α,β-Unsaturated Carbonyl Compounds [J] . Annamaria Deagostino, Cristina Prandi, Paolo Venturello Organic letters . 2003,第21期

机译：1-烷-1,3-二烯的钯催化的Heck反应：α，β-不饱和羰基化合物的区域选择性γ-芳基化
3. THE PALLADIUM-CATALYSED VINYLIC SUBSTITUTION OF VINYL TRIFLATES WITH BETA-SUBSTITUTED-ALPHA,BETA-UNSATURATED CARBONYL COMPOUNDS - AN APPLICATION TO THE SYNTHESIS OF CARDENOLIDES [J] . Arcadi A., Fabrizi G., Marinelli F., Tetrahedron . 1996,第20期

机译：含β-取代的α-贝塔不饱和羰基化合物的三氟乙烯磺酸盐被钯催化的乙烯基取代-在合成硬脂酸中的应用
4. Control over Site of Alkylation in Palladium and Platinum Complexes Bearing alpha,beta-Unsaturated Carbonyl Compounds [C] . Katsuharu Inoue, Masaki Morita, Sensuke Ogoshi, Symposium on Organometallic Chemistry . 2004

机译：控制含有α，β-不饱和羰基化合物的钯和铂复合物中烷基化位点
5. I. Multicatalysis: Development of a Bismuth(III) triflate-catalyzed Nucleophilic addition/ Hydrofunctionalization Reaction in the Synthesis of Complex Heterocycles II. C--H Arylation of Arenes and Heteroarenes with Palladium-Carboxylate Catalysts: Identification of the Catalyst Resting State and the Crucial Role of Pivalate Ligand in Stabilization of the Catalyst III. C--H Arylation of Heteroarenes with Palladium-Carboxylate Catalysts: Importance of Phosphine Ligand for Basic Heteroarene Substrates IV. C--H Arylation of Heteroarenes with Palladium-Carboxylate Catalysts: Effect of the Properties of Basic Heteroarene Substrates on Direct Arylations. [D] . Tundel, Rachel E. 2011

机译：I.多催化作用：在复杂的杂环化合物的合成中三氟甲磺酸铋（III）催化的亲核加成/加氢官能化反应的发展。羰基钯催化剂对芳烃和杂芳烃的CH-H芳基化反应：催化剂静止状态的鉴定以及新戊酸酯配体在稳定催化剂中的关键作用III。羰基钯催化剂催化杂芳烃的CH芳基化：膦配体对基础杂芳烃基质的重要性IV。杂芳烃与钯-羧酸酯的CH芳基化：碱性杂芳烃底物性能对直接芳基化的影响。
6. Copper-Catalyzed β-Boration of αβ-Unsaturated Carbonyl Compounds with Tetrahydroxydiborane [O] . Gary A. Molander, Silas A. McKee -1

机译：铜催化αβ-硼化β不饱和羰基化合物与Tetrahydroxydiborane
7. 1, 4-Addition of Arylboronic Acids and Arylsiloxanes to a, b-Unsaturated Carbonyl Compounds via Transmetalation to Dicationic Palladium(II) Complexes [O] . -1

机译：1,4-通过透射型钯（II）配合物，将芳基硼酸和芳基硼酸和芳基硅氧烷加入A，B-不饱和羰基化合物中

Tandem β-boration/arylation of α,β-unsaturated carbonyl compounds by using a single palladium complex to catalyse both steps

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