(1,n) annulation reactions using (de)-hydrogenative coupling with alcohols or diols represent a straightforward technique for the synthesis of cyclic moieties. Utilization of such renewable resources for chemical transformations in a one-pot manner is the main focus, which avoids generation of stoichiometric waste. Application of such (1,n) annulation approaches drives the catalysis research in a more sustainable way and generates dihydrogen and water as by-products. This feature article highlights the recent (from 2015 to March 2021) progress in the synthesis of stereo-selective cycloalkanes and cycloalkenes, saturated and unsaturated N-heterocycles (cyclic amine, imide, lactam, tetrahydro β-carboline, quinazoline, quinazolinone, 1,3,5-triazines etc.) and other N-heterocycles with the formation of multiple bonds in a one pot operation. Mechanistic studies, new catalytic approaches, and synthetic applications including drug synthesis and post-drug derivatization, scope, and limitations are discussed.