deletedocs.user.js

// ==UserScript==
// @name         Google Docs SHIFT+D Delete
// @namespace    http://tampermonkey.net/
// @version      0.1
// @description  Use SHIFT+D to delete files fast
// @author       Inkh Su Tesou
// @match        https://docs.google.com/document/*
// @grant        none
// ==/UserScript==

(function() {
	console.log( ` - Delete files with SHIFT+D` )

	const simulateMouseEvent = function ( element, eventName ) {
        const bbox = element.getBoundingClientRect(),
              clientX = bbox.left + ( bbox.right - bbox.left ) / 2,
              clientY = bbox.top + ( bbox.bottom - bbox.top ) / 2

		element.dispatchEvent( new MouseEvent( eventName, {
			view : window,
			bubbles : true,
			cancelable : true,
			clientX,
			clientY,
			button : 0
		} ) )
	}

	let target
	let onkeypress = e => {
		if ( e.which !== 68 || !e.shiftKey ) { return }
		while ( !target.classList.contains( `docs-homescreen-list-item` ) ) { target = target.parentNode }
		const parent = target
		const menuToggle = target.querySelector( `[aria-label="More actions. Popup button."]` )
		menuToggle.click()
		let i = 0
		console.log( parent )
		Array.from( parent.querySelectorAll( `div` ) ).forEach( node => {
			if ( node.innerHTML === `Remove` ) {
				const toClick = node.parentNode.parentNode.parentNode.parentNode
				console.log( node, toClick )
                simulateMouseEvent ( toClick, `mousedown` )
                simulateMouseEvent ( toClick, `mouseup` )
                simulateMouseEvent ( toClick, `click` )
                document.querySelector('[name="moveToTrash"]').click()
			}
		} )
	}
	let onmousemove = e => {
		target = e.target
	}
	document.body.addEventListener( `mousemove`, onmousemove, false )
	document.body.addEventListener( `keypress`, onkeypress, false )
})();