Pretransmetalation Intermediates in Suzuki-Miyaura Cross- Couplings: Synthesis of Csp3-, Csp2-and Csp-Organopalladium(II) Boronates

被引：6

作者：

Olding, Angus ^{[1
]}

Ho, Curtis C. ^{[1
]}

Lucas, Nigel T. ^{[2
]}

Bissember, Alex C. ^{[1
]}

机构：

[1] Univ Tasmania UTAS, Sch Nat Sci Chem, Hobart, Tas 7001, Australia

[2] Univ Otago, Dept Chem, Dunedin 9054, Otago, New Zealand

来源：

INORGANIC CHEMISTRY | 2023年 / 62卷 / 13期

基金：

澳大利亚研究理事会;

关键词：

OXIDATIVE-ADDITION; ALKYL BROMIDES; COMPLEXES; TRANSMETALATION; LIGANDS; HALIDES; MILD;

D O I：

10.1021/acs.inorgchem.3c00198

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Organopalladium(II) boronates represent fundamental pretransmetalation intermediates in Suzuki-Miyaura cross-couplings. These species are typically kinetically unstable, making them particularly elusive. In this study, a range of unprecedented, kinetically stable alkyl-, alkenyl-, allenyl-, and alkynylpalladium(II) boronates were prepared from various Csp3, Csp2, and Csp electrophiles via a simple, general method. The structures of these complexes were secured by X-ray crystallography, and the chemical competence of a number of these intermediates in transmetalation was demonstrated.

引用

页码：5054 / 5057

页数：4

共 15 条

[1] Suzuki-Miyaura Csp2-Csp2 Cross-Couplings Employing Nickel(II) Pincer Precatalysts: Mechanistic Investigations
Ho, Curtis C.
Olding, Angus
Fuller, Rebecca O.
Canty, Allan J.
Lucas, Nigel T.
Bissember, Alex C.
ORGANOMETALLICS, 2021, 40 (14) : 2305 - 2310
[2] Suzuki-Miyaura Cross-Couplings of Alkylboranes: Transmetalation Studies and Synthesis of Model Organopalladium Pretransmetalation Species
Olding, Angus
Ho, Curtis C.
Lucas, Nigel T.
Yates, Brian F.
Canty, Allan J.
Bissember, Alex C.
ACS CATALYSIS, 2024, 14 (21): : 15946 - 15955
[3] Pretransmetalation Intermediates in Suzuki-Miyaura C-C and Carbonylative Cross-Couplings: Synthesis and Structural Authentication of Aryl- and Aroylnickel(II) Boronates
Bissember, Alex C.
Olding, Angus
Ho, Curtis C.
Lucas, Nigel T.
Canty, Allan J.
ACS CATALYSIS, 2023, 13 (05) : 3153 - 3157
[4] Stereospecific Csp3 Suzuki-Miyaura Cross-Coupling That Evades β-Oxygen Elimination
LaPorte, Antonio J.
Shi, Yao
Hein, Jason E.
Burke, Martin D.
ACS CATALYSIS, 2022, 12 (17): : 10905 - 10912
[5] Synthesis of PdII Triazolylidene Complexes via an Unusual Csp2-Csp2 Decoupling Reaction: Applications in α-Arylation of Amide and Suzuki-Miyaura Coupling Reactions
Naskar, Rajat
Sinhababu, Saptaparna
Majumder, Adhir
Maity, Ramananda
CHEMISTRYSELECT, 2022, 7 (27):
[6] Chromium(II)-Catalyzed Diastereoselective and Chemoselective Csp2-Csp3 Cross-Couplings Using Organomagnesium Reagents
Li, Jie
Ren, Qianyi
Cheng, Xinyi
Karaghiosoff, Konstantin
Knochel, Paul
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (45) : 18127 - 18135
[7] Axial shielding of Pd(II) complexes enables perfect stereoretention in Suzuki-Miyaura cross-coupling of Csp3 boronic acids
Jonathan W. Lehmann
Ian T. Crouch
Daniel J. Blair
Melanie Trobe
Pulin Wang
Junqi Li
Martin D. Burke
Nature Communications, 10
[8] Axial shielding of Pd(II) complexes enables perfect stereoretention in Suzuki-Miyaura cross-coupling of Csp3 boronic acids
Lehmann, Jonathan W.
Crouch, Ian T.
Blair, Daniel J.
Trobe, Melanie
Wang, Pulin
Li, Junqi
Burke, Martin D.
NATURE COMMUNICATIONS, 2019, 10
[9] Increasing saturation: development of broadly applicable photocatalytic Csp2-Csp3 cross-couplings of alkyl trifluoroborates and (hetero)aryl bromides for array synthesis
Cauley, Anthony N.
Sezen-Edmonds, Melda
Simmons, Eric M.
Cavallaro, Cullen L.
REACTION CHEMISTRY & ENGINEERING, 2021, 6 (09): : 1666 - 1676
[10] Synthesis and characterization of sterically hindered thiolate Pd(II) complexes of the type [Pd(SR)2(TMEDA)]: Examination of their catalytic properties in phosphane-free Suzuki-Miyaura cross couplings
Basauri-Molina, Manuel
Hernandez-Ortega, Simon
Toscano, Ruben A.
Valdes-Martinez, Jesus
Morales-Morales, David
INORGANICA CHIMICA ACTA, 2010, 363 (06) : 1222 - 1229

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