Modular Synthesis of (Borylmethyl)silanes through Orthogonal Functionalization of a Carbon Atom

被引：1

作者：

Chowdhury, Rajdip ^{[1
]}

Elek, Gabor Zoltan ^{[1
,2
]}

Meana-Baamonde, Beatriz ^{[1
,3
]}

Mendoza, Abraham ^{[1
,3
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

[2] Tallinn Univ Technol, Dept Chem & Biotechnol, EE-12618 Tallinn, Estonia

[3] Univ Valencia, Inst Mol Sci ICMol, Paterna 46980, Spain

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 11期

基金：

瑞典研究理事会; 欧洲研究理事会;

关键词：

H INSERTION REACTION; C(SP(3))-H BORYLATION; CARBENE INSERTION; CROSS-COUPLINGS; BOND FORMATION; SILICON; ESTERS; COPPER;

D O I：

10.1021/acs.orglett.3c00474

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(Borylmethyl)trimethylsilanes are important build-ing blocks in organic synthesis displaying a unique reactivity. Yet, the synthesis of more advanced derivatives is limited by the advanced silicon intermediates required for their preparation. Herein, a one-pot synthesis of (borylmethyl)silanes is developed, sourced on available alkyl-, aryl-, alkoxy-, aryloxy-, and silyl-hydrosilane materials. The privileged reactivity of N-hydroxyph-thalimidyl diazoacetate (NHPI-DA) in Si-H insertion and alpha-silyl redox-active esters in different decarboxylative borylation reactions are scrutinized.

引用

页码：1935 / 1940

页数：6

共 50 条

[1] Synthesis of carbaporphyrins and functionalization of the interior carbon atom.
Spence, JD
Hayes, MJ
Lash, TD
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U588 - U588
[2] Modular Synthesis, Orthogonal Post-Functionalization, Absorption, and Chiroptical Properties of Cationic [6]Helicenes
Torricelli, Franck
Bosson, Johann
Besnard, Celine
Chekini, Mahshid
Buergi, Thomas
Lacour, Jerome
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (06) : 1796 - 1800
[3] Modular Functionalization of Carbon Nanotubes and Fullerenes
Zhang, Wei
Sprafke, Johannes K.
Ma, Minglin
Tsui, Emily Y.
Sydlik, Stefanie A.
Rutledge, Gregory C.
Swager, Timothy M.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (24) : 8446 - 8454
[4] Functionalization of carbon nanotubes:: Single atom adsorption
Gülseren, U
Dag, S
Durgun, E
Yildirim, T
Ciraci, S
[J]. NANOENGINEERED NANOFIBROUS MATERIALS, 2004, 169 : 165 - 173
[5] Alternating Terpolymers through Cyclopolymerization and Subsequent Orthogonal Functionalization
Gerdt, Philipp
Studer, Armido
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (39)
[6] Modular and orthogonal synthesis of hybrid polymers and networks
Liu, Shuang
Dicker, Kevin T.
Jia, Xinqiao
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (25) : 5218 - 5237
[7] Versatile surface functionalization of cellulose through modular chemistry
Moran-Mirabal, Jose
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[8] A Modular Synthesis of Some Biologically Relevant Cyclic Peptides through Late-Stage Functionalization
Mukherjee, Jyoti Prasad
Sil, Suman
Pahari, Amit K.
Chattopadhyay, Shital K.
[J]. SYNTHESIS-STUTTGART, 2016, 48 (08): : 1181 - 1190
[9] Functionalization of Carbon Particles by Atom Transfer Radical Polymerization
Nurettin Sahiner
Sultan B. Sengel
[J]. MRS Advances, 2017, 2 (47) : 2537 - 2544
[10] Reactions of Titanium Hydrazides with Silanes and Boranes: N-N Bond Cleavage and N Atom Functionalization
Stevenson, Laura C.
Mellino, Simona
Clot, Eric
Mountford, Philip
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (32) : 10140 - 10143

← 1 2 3 4 5 →