NMR filesThis record supports 'Iterative reactions of transient boronic acids enable sequential C-C bond formation', which has been published in Nature Chemistry.This work was supported by the EPSRC [grant numbers EP/K009494/1 and EP/M004120/1]

A Bonet

AJ Hunt

Andreas Hafner

C Liu

CCC Johansson-Seechurn

Claudio Battilocchio

Daniel M. Allwood

David C. Blakemore

DG Hall

DM Allwood

DN Tran

DS Matteson

Duc N. Tran

EM Woerly

Florian Feist

HR Snyder

J Barluenga

J Hartwig

J Li

J Sun

JC Lo

JC Tellis

L Kupracz

M Burns

M Raducan

MA Molander

Meike Simon

N Miyaura

R Jana

R Kumara

R Rasappan

RJ Phipps

S Balieu

S Nakagawa

S Roesner

SN Mlynarski

Steven V. Ley

T Esumi

The ability to form multiple carbon–carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions have dominated in the development of C–C bond forming processes. A desire to reduce the reliance on precious metals and a need to obtain products with very low levels of metal impurities has brought a renewed focus on metal-free coupling processes. Here, we report the in situ preparation of reactive allylic and benzylic boronic acids, obtained by reacting flow-generated diazo compounds with boronic acids, and their application in controlled iterative C–C bond forming reactions is described. Thus far we have shown the formation of up to three C–C bonds in a sequence including the final trapping of a reactive boronic acid species with an aldehyde to generate a range of new chemical structures

Battilocchio, Claudio

Feist, Florian

Hafner, Andreas

Simon, Meike

Tran, Duc

Allwood, Daniel

Blakemore, David

Ley, Steven

Sheffield Hallam University Research Archive

Iterative reactions of transient boronic acids enable sequential C–C bond formation

Crossref

Nature Chemistry

The ability to form multiple carbon-carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions have dominated in the development of C-C bond forming processes. A desire to reduce the reliance on precious metals and a need to obtain products with very low levels of metal impurities has brought a renewed focus on metal-free coupling processes. Here, we report the in situ preparation of reactive allylic and benzylic boronic acids, obtained by reacting flow-generated diazo compounds with boronic acids, and their application in controlled iterative C-C bond forming reactions is described. Thus far we have shown the formation of up to three C-C bonds in a sequence including the final trapping of a reactive boronic acid species with an aldehyde to generate a range of new chemical structures.We are grateful to Pfizer (C.B., D.M.A., D.C.B. and J.M.H.), the Studienstiftung des deutschen Volkes  (German  National  Academic  Foundation,  F.F.),  the  Alexander-von-Humboldt  foundation  (A.H.),  Erasmus+  (M.S.),  the  Swiss  National  Science  Foundation  (D.N.T.)  and  the  EPSRC  (S.V.L.,  grant  n°  EP/K009494/1  and  EP/M004120/1)  for  financial  support. We  would  also  like  to  thank  Dr  Richard  Turner for providing assistance throughout the development of the research programme.This is the author accepted manuscript. The final version is available from Nature Publishing Group via http://dx.doi.org/10.1038/nchem.243

Tran, Duc N

Allwood, Daniel M

Blakemore, David C

Ley, Steven V

Apollo (Cambridge)

Iterative reactions of transient boronic acids enable sequential C-C bond formation.

Tran, Duc. N.

Allwood, Daniel. M.

Blakemore, David. C.

Ley, Steven V.