Secondary Amines via Alkyl Azides

[Rhodium]

This looks like a much more versatile and user-friendly route than the one posted in

Post 210412

(foxy2: "MDE from Safrole Azide", Novel Discourse)
It also seems to be related to the procedure mentioned in

Post 325198

(Ritter: "Azides--> N-Methylamines", Novel Discourse)

A Convergent One-Pot Synthesis of Secondary Amines via Aza-Wittig Reaction
Tadeusz Gajda, Anna Koziara, Krystyna Osowska-Pacewicka, Stefan Zawadzki, Andrzej Zwierzak

Synthetic Communications, 22(13), 1929-1938 (1992)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/aza-wittig.html)

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Abstract
Secondary amines are obtained in moderate-good yields by reduction of crude imines prepared from N-alkyltriethoxyiminophosphoranes and aldehydes via the aza-Wittig reaction. N-Alkyltriethoxyiminophosphoranes are synthesized by one-pot azidation of alkyl bromides followed by Staudinger reaction.

[Rhodium]

One-Pot Conversion Of Alkyl Bromides Into Imines Via The Staudinger Reaction
Petr Vanek & Petr Klán

Synth. Commun. 30(, 1503-1507 (2000)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/aza-wittig.html#imine)

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Abstract
A new one-pot procedure for transforming primary alkyl bromides into the corresponding imines via the Staudinger reaction has been developed. Acetonitrile was found to be an excellent solvent for azidation as well as the reaction of organic azide with triphenylphosphine and a carbonyl compound.

[Rhodium]

A One-Pot Aza-Wittig Based Solution and Polymer Supported Route to Amines
K. Hemming, M. J. Bevan, C. Loukou, S. D. Patel, D. Renaudeau

Synlett 1565-1568 (2000)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/aza-wittig.html#onepotpoly)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000472833-aza-wittig_fig1.gif" target="_blank" title="View this image">

Abstract
This paper presents a high yielding one-pot solution phase and polymer supported synthesis of a range of primary and secondary amines starting from azides and aldehydes. The synthesis utilises a tandem process which begins with an aza-Wittig reaction between the aldehyde and an iminophosphorane, followed by reduction, or organometallic 1,2-addition reaction, of the resultant imine. The requisite iminophosphoranes were accessed using the highly efficient Staudinger reaction between the azide starting material and a phosphine. The process was applicable to the solid phase by the use of polymer supported iminophosphoranes and polymer supported cyanoborohydride.

[psychokitty]

The following PDF is a review of Azide chemistry:

Azides: Their Preparation and Synthetic Uses
Eric F. V. Scriven & Kenneth Turnbull
Chemical Reviews, Vol. 88, No. 2, p. 297- (1988)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000472833-Azides_-_Their_Preparation_and_Synthetic_Uses.pdf" target="_blank" title="Download this file">