Reactions of aminoboron compounds with palladium and platinum complexes

Christopher M. Vogels; Heather L. Wellwood; Kumar Biradha; Michael J. Zaworotko; Stephen A. Westcott

doi:10.1139/v99-106

Reactions of aminoboron compounds with palladium and platinum complexes

Christopher M. Vogels
, Heather L. Wellwood
, Kumar Biradha
, Michael J. Zaworotko
, Stephen A. Westcott

Research output: Contribution to journal › Article › peer-review

Abstract

Reactions of 3-NH₂C₆H₄B(OH)₂ (1, APBA) with [MCl₄]^2- (M = Pd, Pt) give the boronic acid-containing complexes, MCl₂(APBA)₂ (M = Pd, 2; M = Pt, 3). Addition of 1 to [PdCl₂(COE)]₂ (COE = η²-C₈H₁₄) ultimately led to PdCl₂(APBA)₂ (2). The pinacol derivative PdCl₂(APBpin)₂ (5, pin = O₂C₂Me₄) was characterized by an X-ray diffraction study. Crystals of 5 were monoclinic, a = 13.836(5), b = 14.937(5), c = 11.287(5) A, β = 99.042(9)°, Z = 2, with space group P2₁/c. Monoalkene complexes PtCl₂(COE)(APBA) (8) and PtCl₂(COE)(APBpin) (9) were generated from the addition of APBA and APBpin, respectively, to [PtCl₂(COE)]₂. Reactions of 2-NMe₂CH₂C₆H₄B(OH)₂ (10) with palladium complex [PdCl₂(COE)]₂ proceed via selective B - C bond cleavage to give the cyclopalladated dimer [PdCl(2-NMe₂CH₂C₆H₄)]₂ as the major amine-containing product. Likewise, reactions with borinic esters H₂NCH₂CH₂OBR₂ (R = Bu, 14; R = Ph, 15) give products derived from cleavage of the B - O bond. The unique palladium complex PdCl₂[3-NC₅H₄B(OH)₂]₂ (19) was prepared by addition of (3-NC₅H₄BEt₂)₄ (18) to [PdCl₂(COE)]₂ in wet methylene chloride, where adventitious water was used to convert the organoborane product into the corresponding boronic acid moiety.

Original language	English
Pages (from-to)	1196-1207
Number of pages	12
Journal	Canadian Journal of Chemistry
Volume	77
Issue number	7
DOIs	https://doi.org/10.1139/v99-106
Publication status	Published - 1999
Externally published	Yes

Keywords

Aminoboronic acids
Cyclometallation
Palladium
Platinum

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10.1139/v99-106

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@article{5394ee6c9ebb44d0a3c52f8c22a6099c,

title = "Reactions of aminoboron compounds with palladium and platinum complexes",

abstract = "Reactions of 3-NH2C6H4B(OH)2 (1, APBA) with [MCl4]2- (M = Pd, Pt) give the boronic acid-containing complexes, MCl2(APBA)2 (M = Pd, 2; M = Pt, 3). Addition of 1 to [PdCl2(COE)]2 (COE = η2-C8H14) ultimately led to PdCl2(APBA)2 (2). The pinacol derivative PdCl2(APBpin)2 (5, pin = O2C2Me4) was characterized by an X-ray diffraction study. Crystals of 5 were monoclinic, a = 13.836(5), b = 14.937(5), c = 11.287(5) A, β = 99.042(9)°, Z = 2, with space group P21/c. Monoalkene complexes PtCl2(COE)(APBA) (8) and PtCl2(COE)(APBpin) (9) were generated from the addition of APBA and APBpin, respectively, to [PtCl2(COE)]2. Reactions of 2-NMe2CH2C6H4B(OH)2 (10) with palladium complex [PdCl2(COE)]2 proceed via selective B - C bond cleavage to give the cyclopalladated dimer [PdCl(2-NMe2CH2C6H4)]2 as the major amine-containing product. Likewise, reactions with borinic esters H2NCH2CH2OBR2 (R = Bu, 14; R = Ph, 15) give products derived from cleavage of the B - O bond. The unique palladium complex PdCl2[3-NC5H4B(OH)2]2 (19) was prepared by addition of (3-NC5H4BEt2)4 (18) to [PdCl2(COE)]2 in wet methylene chloride, where adventitious water was used to convert the organoborane product into the corresponding boronic acid moiety.",

keywords = "Aminoboronic acids, Cyclometallation, Palladium, Platinum",

author = "Vogels, \{Christopher M.\} and Wellwood, \{Heather L.\} and Kumar Biradha and Zaworotko, \{Michael J.\} and Westcott, \{Stephen A.\}",

year = "1999",

doi = "10.1139/v99-106",

language = "English",

volume = "77",

pages = "1196--1207",

journal = "Canadian Journal of Chemistry",

issn = "0008-4042",

number = "7",

}

TY - JOUR

T1 - Reactions of aminoboron compounds with palladium and platinum complexes

AU - Vogels, Christopher M.

AU - Wellwood, Heather L.

AU - Biradha, Kumar

AU - Zaworotko, Michael J.

AU - Westcott, Stephen A.

PY - 1999

Y1 - 1999

N2 - Reactions of 3-NH2C6H4B(OH)2 (1, APBA) with [MCl4]2- (M = Pd, Pt) give the boronic acid-containing complexes, MCl2(APBA)2 (M = Pd, 2; M = Pt, 3). Addition of 1 to [PdCl2(COE)]2 (COE = η2-C8H14) ultimately led to PdCl2(APBA)2 (2). The pinacol derivative PdCl2(APBpin)2 (5, pin = O2C2Me4) was characterized by an X-ray diffraction study. Crystals of 5 were monoclinic, a = 13.836(5), b = 14.937(5), c = 11.287(5) A, β = 99.042(9)°, Z = 2, with space group P21/c. Monoalkene complexes PtCl2(COE)(APBA) (8) and PtCl2(COE)(APBpin) (9) were generated from the addition of APBA and APBpin, respectively, to [PtCl2(COE)]2. Reactions of 2-NMe2CH2C6H4B(OH)2 (10) with palladium complex [PdCl2(COE)]2 proceed via selective B - C bond cleavage to give the cyclopalladated dimer [PdCl(2-NMe2CH2C6H4)]2 as the major amine-containing product. Likewise, reactions with borinic esters H2NCH2CH2OBR2 (R = Bu, 14; R = Ph, 15) give products derived from cleavage of the B - O bond. The unique palladium complex PdCl2[3-NC5H4B(OH)2]2 (19) was prepared by addition of (3-NC5H4BEt2)4 (18) to [PdCl2(COE)]2 in wet methylene chloride, where adventitious water was used to convert the organoborane product into the corresponding boronic acid moiety.

AB - Reactions of 3-NH2C6H4B(OH)2 (1, APBA) with [MCl4]2- (M = Pd, Pt) give the boronic acid-containing complexes, MCl2(APBA)2 (M = Pd, 2; M = Pt, 3). Addition of 1 to [PdCl2(COE)]2 (COE = η2-C8H14) ultimately led to PdCl2(APBA)2 (2). The pinacol derivative PdCl2(APBpin)2 (5, pin = O2C2Me4) was characterized by an X-ray diffraction study. Crystals of 5 were monoclinic, a = 13.836(5), b = 14.937(5), c = 11.287(5) A, β = 99.042(9)°, Z = 2, with space group P21/c. Monoalkene complexes PtCl2(COE)(APBA) (8) and PtCl2(COE)(APBpin) (9) were generated from the addition of APBA and APBpin, respectively, to [PtCl2(COE)]2. Reactions of 2-NMe2CH2C6H4B(OH)2 (10) with palladium complex [PdCl2(COE)]2 proceed via selective B - C bond cleavage to give the cyclopalladated dimer [PdCl(2-NMe2CH2C6H4)]2 as the major amine-containing product. Likewise, reactions with borinic esters H2NCH2CH2OBR2 (R = Bu, 14; R = Ph, 15) give products derived from cleavage of the B - O bond. The unique palladium complex PdCl2[3-NC5H4B(OH)2]2 (19) was prepared by addition of (3-NC5H4BEt2)4 (18) to [PdCl2(COE)]2 in wet methylene chloride, where adventitious water was used to convert the organoborane product into the corresponding boronic acid moiety.

KW - Aminoboronic acids

KW - Cyclometallation

KW - Palladium

KW - Platinum

UR - https://www.scopus.com/pages/publications/0033306383

U2 - 10.1139/v99-106

DO - 10.1139/v99-106

M3 - Article

AN - SCOPUS:0033306383

SN - 0008-4042

VL - 77

SP - 1196

EP - 1207

JO - Canadian Journal of Chemistry

JF - Canadian Journal of Chemistry

IS - 7

ER -

Reactions of aminoboron compounds with palladium and platinum complexes

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Keywords

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