共 34 条
Direct Observation of C-H Cyclopalladation at Tertiary Positions Enabled by an Exo-Directing Group
被引:30
作者:

Ren, Zhi
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Texas Austin, Dept Chem, Austin, TX 78712 USA Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

Dong, Guangbin
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Texas Austin, Dept Chem, Austin, TX 78712 USA Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
机构:
[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
关键词:
CATALYZED DIRECT ARYLATION;
QUATERNARY CARBON CENTERS;
INSERTION REACTIONS;
PALLADIUM;
BOND;
FUNCTIONALIZATION;
ACTIVATION;
REACTIVITY;
CYCLOPROPANES;
ME;
D O I:
10.1021/acs.organomet.6b00185
中图分类号:
O61 [无机化学];
学科分类号:
070301 ;
081704 ;
摘要:
Here we describe the first preparation of tertiary alkyl palladium complexes via C-H activation. Enabled by an exo-type oxime directing group, cyclopalladation occurred smoothly at the bridgehead position. Treatment of the resulting complex with iodine led to C-H iodination at the methine carbon. This study provides important mechanistic information for palladium-catalyzed functionalization of methine C-H bonds.
引用
收藏
页码:1057 / 1059
页数:3
相关论文
共 34 条
[11]
Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds
[J].
Daugulis, Olafs
;
Do, Hien-Quang
;
Shabashov, Dmitry
.
ACCOUNTS OF CHEMICAL RESEARCH,
2009, 42 (08)
:1074-1086

Daugulis, Olafs
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Houston, Dept Chem, Houston, TX 77204 USA Univ Houston, Dept Chem, Houston, TX 77204 USA

Do, Hien-Quang
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Houston, Dept Chem, Houston, TX 77204 USA Univ Houston, Dept Chem, Houston, TX 77204 USA

Shabashov, Dmitry
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Houston, Dept Chem, Houston, TX 77204 USA Univ Houston, Dept Chem, Houston, TX 77204 USA
[12]
Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions
[J].
Engle, Keary M.
;
Mei, Tian-Sheng
;
Wasa, Masayuki
;
Yu, Jin-Quan
.
ACCOUNTS OF CHEMICAL RESEARCH,
2012, 45 (06)
:788-802

Engle, Keary M.
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

Mei, Tian-Sheng
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

Wasa, Masayuki
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

Yu, Jin-Quan
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[13]
Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity
[J].
Giri, Ramesh
;
Shi, Bing-Feng
;
Engle, Keary M.
;
Maugel, Nathan
;
Yu, Jin-Quan
.
CHEMICAL SOCIETY REVIEWS,
2009, 38 (11)
:3242-3272

Giri, Ramesh
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

Shi, Bing-Feng
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

Engle, Keary M.
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

Maugel, Nathan
论文数: 0 引用数: 0
h-index: 0
机构:
Brandeis Univ, Dept Chem, Waltham, MA 02453 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

Yu, Jin-Quan
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[14]
Pd(II)-Catalyzed Alkylation of Tertiary Carbon via Directing-Group-Mediated C(sp3)-H Activation: Synthesis of Chiral 1,1,2-Trialkyl Substituted Cyclopropanes
[J].
Hoshiya, Naoyuki
;
Takenaka, Kei
;
Shuto, Satoshi
;
Uenishi, Jun'ichi
.
ORGANIC LETTERS,
2016, 18 (01)
:48-51

Hoshiya, Naoyuki
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Pharmaceut Univ, Dept Pharmaceut Chem, Yamashina Ku, Kyoto 6078412, Japan Kyoto Pharmaceut Univ, Dept Pharmaceut Chem, Yamashina Ku, Kyoto 6078412, Japan

Takenaka, Kei
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Pharmaceut Univ, Dept Pharmaceut Chem, Yamashina Ku, Kyoto 6078412, Japan Kyoto Pharmaceut Univ, Dept Pharmaceut Chem, Yamashina Ku, Kyoto 6078412, Japan

Shuto, Satoshi
论文数: 0 引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
Hokkaido Univ, Ctr Res & Educ Drug Discovery, Kita Ku, Sapporo, Hokkaido 0600812, Japan Kyoto Pharmaceut Univ, Dept Pharmaceut Chem, Yamashina Ku, Kyoto 6078412, Japan

Uenishi, Jun'ichi
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Pharmaceut Univ, Dept Pharmaceut Chem, Yamashina Ku, Kyoto 6078412, Japan Kyoto Pharmaceut Univ, Dept Pharmaceut Chem, Yamashina Ku, Kyoto 6078412, Japan
[15]
Palladium-Catalyzed Arylation of Cyclopropanes via Directing Group-Mediated C(sp3)-H Bond Activation To Construct Quaternary Carbon Centers: Synthesis of cis- and trans-1,1,2-Trisubstituted Chiral Cyclopropanes
[J].
Hoshiya, Naoyuki
;
Kobayashi, Takaaki
;
Arisawa, Mitsuhiro
;
Shuto, Satoshi
.
ORGANIC LETTERS,
2013, 15 (24)
:6202-6205

Hoshiya, Naoyuki
论文数: 0 引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

Kobayashi, Takaaki
论文数: 0 引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

Arisawa, Mitsuhiro
论文数: 0 引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

Shuto, Satoshi
论文数: 0 引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
Hokkaido Univ, Ctr Res & Educ Drug Dev, Kita Ku, Sapporo, Hokkaido 0600812, Japan Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
[16]
Silver-Promoted, Palladium-Catalyzed Direct Arylation of Cyclopropanes: Facile Access to Spiro 3,3′-Cyclopropyl Oxindoles
[J].
Ladd, Carolyn L.
;
Roman, Daniela Sustac
;
Charette, Andre B.
.
ORGANIC LETTERS,
2013, 15 (06)
:1350-1353

Ladd, Carolyn L.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Ctr Green Chem & Catalysis, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Ctr Green Chem & Catalysis, Montreal, PQ H3C 3J7, Canada

Roman, Daniela Sustac
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Ctr Green Chem & Catalysis, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Ctr Green Chem & Catalysis, Montreal, PQ H3C 3J7, Canada

Charette, Andre B.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Ctr Green Chem & Catalysis, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Ctr Green Chem & Catalysis, Montreal, PQ H3C 3J7, Canada
[17]
Benziporphyrins, a unique platform for exploring the aromatic characteristics of porphyrinoid systems
[J].
Lash, Timothy D.
.
ORGANIC & BIOMOLECULAR CHEMISTRY,
2015, 13 (29)
:7846-7878

Lash, Timothy D.
论文数: 0 引用数: 0
h-index: 0
机构:
Illinois State Univ, Dept Chem, Normal, IL 61790 USA Illinois State Univ, Dept Chem, Normal, IL 61790 USA
[18]
Unexpected Alkyl Group Migration in Palladium(II) Benzocarbaporphyrins
[J].
Lash, Timothy D.
.
ORGANIC LETTERS,
2011, 13 (17)
:4632-4635

Lash, Timothy D.
论文数: 0 引用数: 0
h-index: 0
机构:
Illinois State Univ, Dept Chem, Normal, IL 61790 USA Illinois State Univ, Dept Chem, Normal, IL 61790 USA
[19]
From C(sp2)-H to C(sp3)-H: systematic studies on transition metal-catalyzed oxidative C-C formation
[J].
Li, Bi-Jie
;
Shi, Zhang-Jie
.
CHEMICAL SOCIETY REVIEWS,
2012, 41 (17)
:5588-5598

Li, Bi-Jie
论文数: 0 引用数: 0
h-index: 0
机构:
Peking Univ, BNLMS, Beijing 100871, Peoples R China
Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem, Beijing 100871, Peoples R China
Peking Univ, Green Chem Ctr, Beijing 100871, Peoples R China Peking Univ, BNLMS, Beijing 100871, Peoples R China

Shi, Zhang-Jie
论文数: 0 引用数: 0
h-index: 0
机构:
Peking Univ, BNLMS, Beijing 100871, Peoples R China
Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem, Beijing 100871, Peoples R China
Peking Univ, Green Chem Ctr, Beijing 100871, Peoples R China
Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China Peking Univ, BNLMS, Beijing 100871, Peoples R China
[20]
Synthesis and Reactivity of Carbachlorins and Carbaporphyrins
[J].
Li, Daming
;
Lash, Timothy D.
.
JOURNAL OF ORGANIC CHEMISTRY,
2014, 79 (15)
:7112-7121

Li, Daming
论文数: 0 引用数: 0
h-index: 0
机构:
Illinois State Univ, Dept Chem, Normal, IL 61790 USA Illinois State Univ, Dept Chem, Normal, IL 61790 USA

Lash, Timothy D.
论文数: 0 引用数: 0
h-index: 0
机构:
Illinois State Univ, Dept Chem, Normal, IL 61790 USA Illinois State Univ, Dept Chem, Normal, IL 61790 USA